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<span>Approaches</span> </div> </a> <button aria-controls="toc-Approaches-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Approaches subsection</span> </button> <ul id="toc-Approaches-sublist" class="vector-toc-list"> <li id="toc-Enantioselective_catalysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enantioselective_catalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Enantioselective catalysis</span> </div> </a> <ul id="toc-Enantioselective_catalysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chiral_auxiliaries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chiral_auxiliaries"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Chiral auxiliaries</span> </div> </a> <ul id="toc-Chiral_auxiliaries-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biocatalysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biocatalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Biocatalysis</span> </div> </a> <ul id="toc-Biocatalysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enantioselective_organocatalysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enantioselective_organocatalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Enantioselective organocatalysis</span> </div> </a> <ul id="toc-Enantioselective_organocatalysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chiral_pool_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chiral_pool_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Chiral pool synthesis</span> </div> </a> <ul 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</button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Inception_(1815–1905)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inception_(1815–1905)"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Inception (1815–1905)</span> </div> </a> <ul id="toc-Inception_(1815–1905)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Early_work_(1905–1965)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_work_(1905–1965)"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Early work (1905–1965)</span> </div> </a> <ul id="toc-Early_work_(1905–1965)-sublist" class="vector-toc-list"> <li id="toc-Thalidomide" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Thalidomide"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Thalidomide</span> </div> </a> <ul id="toc-Thalidomide-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Modern_age_(since_1965)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Modern_age_(since_1965)"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Modern age (since 1965)</span> </div> </a> <ul id="toc-Modern_age_(since_1965)-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul 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interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/S%C3%ADntesi_asim%C3%A8trica" title="Síntesi asimètrica – Catalan" lang="ca" hreflang="ca" data-title="Síntesi asimètrica" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Asymetrick%C3%A1_synt%C3%A9za" title="Asymetrická syntéza – Czech" lang="cs" hreflang="cs" data-title="Asymetrická syntéza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Enantioselektive_Synthese" title="Enantioselektive Synthese – German" lang="de" hreflang="de" data-title="Enantioselektive Synthese" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/As%C3%BCmmeetriline_s%C3%BCntees" title="Asümmeetriline süntees – Estonian" lang="et" hreflang="et" data-title="Asümmeetriline süntees" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/S%C3%ADntesis_asim%C3%A9trica" title="Síntesis asimétrica – Spanish" lang="es" hreflang="es" data-title="Síntesis asimétrica" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Sintesi_asimetriko" title="Sintesi asimetriko – Basque" lang="eu" hreflang="eu" data-title="Sintesi asimetriko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%86%D8%AA%D8%B2_%D9%86%D8%A7%D9%85%D8%AA%D9%82%D8%A7%D8%B1%D9%86" title="سنتز نامتقارن – Persian" lang="fa" hreflang="fa" data-title="سنتز نامتقارن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Synth%C3%A8se_asym%C3%A9trique" title="Synthèse asymétrique – French" lang="fr" hreflang="fr" data-title="Synthèse asymétrique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B9%84%EB%8C%80%EC%B9%AD_%ED%95%A9%EC%84%B1" title="비대칭 합성 – Korean" lang="ko" hreflang="ko" data-title="비대칭 합성" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Sintesi_asimmetrica" title="Sintesi asimmetrica – Italian" lang="it" hreflang="it" data-title="Sintesi asimmetrica" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Asymmetrische_synthese" title="Asymmetrische synthese – Dutch" lang="nl" hreflang="nl" data-title="Asymmetrische synthese" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E4%B8%8D%E6%96%89%E5%90%88%E6%88%90" title="不斉合成 – Japanese" lang="ja" hreflang="ja" data-title="不斉合成" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Asimmetrik_sintez" title="Asimmetrik sintez – Uzbek" lang="uz" hreflang="uz" data-title="Asimmetrik sintez" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Synteza_asymetryczna" title="Synteza asymetryczna – Polish" lang="pl" hreflang="pl" data-title="Synteza asymetryczna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li 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hreflang="ru" data-title="Стереоселективный синтез" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Asimetri%C4%8Dna_sinteza" title="Asimetrična sinteza – Serbian" lang="sr" hreflang="sr" data-title="Asimetrična sinteza" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Asimetri%C4%8Dna_sinteza" title="Asimetrična sinteza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Asimetrična sinteza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Asymmetrinen_synteesi" title="Asymmetrinen synteesi – Finnish" lang="fi" hreflang="fi" data-title="Asymmetrinen synteesi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Enantioselektiv_reaktion" title="Enantioselektiv reaktion – Swedish" lang="sv" hreflang="sv" data-title="Enantioselektiv reaktion" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Enantiyoselektif_sentez" title="Enantiyoselektif sentez – Turkish" lang="tr" hreflang="tr" data-title="Enantiyoselektif sentez" data-language-autonym="Türkçe" data-language-local-name="Turkish" 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src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Sharpless_Dihydroxylation_Scheme.png/500px-Sharpless_Dihydroxylation_Scheme.png" decoding="async" width="500" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Sharpless_Dihydroxylation_Scheme.png/750px-Sharpless_Dihydroxylation_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Sharpless_Dihydroxylation_Scheme.png/1000px-Sharpless_Dihydroxylation_Scheme.png 2x" data-file-width="1672" data-file-height="507" /></a><figcaption>In the <a href="/wiki/Sharpless_dihydroxylation" class="mw-redirect" title="Sharpless dihydroxylation">Sharpless dihydroxylation</a> reaction the chirality of the product can be controlled by the "<a href="/wiki/AD-mix" title="AD-mix">AD-mix</a>" used. This is an example of enantioselective synthesis using <a href="/wiki/Asymmetric_induction" title="Asymmetric induction">asymmetric induction</a><br /><br />Key: R<sub>L</sub> = Largest substituent; R<sub>M</sub> = Medium-sized substituent; R<sub>S</sub> = Smallest substituent</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Chirality_with_hands.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/300px-Chirality_with_hands.svg.png" decoding="async" width="300" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/450px-Chirality_with_hands.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/600px-Chirality_with_hands.svg.png 2x" data-file-width="765" data-file-height="519" /></a><figcaption>Two enantiomers of a generic <a href="/wiki/Alpha_amino_acid" class="mw-redirect" title="Alpha amino acid">alpha amino acid</a> <style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend"><span class="legend-color mw-no-invert" style="background-color:black; color:white;"> </span> <a href="/wiki/Carbon" title="Carbon">Carbon</a> at the <a href="/wiki/Chiral_center" class="mw-redirect" title="Chiral center">chiral center</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#ff4500; color:black;"> </span> <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a> group</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#00dfff; color:black;"> </span> R group</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:grey; color:black;"> </span> <a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a></div></figcaption></figure> <p><b>Enantioselective synthesis</b>, also called <b>asymmetric synthesis</b>,<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> is a form of <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a>. It is defined by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> as "a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> (or reaction sequence) in which one or more new elements of <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chirality</a> are formed in a substrate molecule and which produces the <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomeric</a> (<a href="/wiki/Enantiomer" title="Enantiomer">enantiomeric</a> or <a href="/wiki/Diastereomer" title="Diastereomer">diastereomeric</a>) products in <a href="/wiki/Enantiomeric_excess" title="Enantiomeric excess">unequal amounts</a>."<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers. </p><p>Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">pharmaceuticals</a>, as the different <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a> or <a href="/wiki/Diastereomer" title="Diastereomer">diastereomers</a> of a molecule often have different <a href="/wiki/Biological_activity" title="Biological activity">biological activity</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Overview">Overview</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=1" title="Edit section: Overview"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Energy_diagram_for_enantioselective_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Energy_diagram_for_enantioselective_synthesis.png/300px-Energy_diagram_for_enantioselective_synthesis.png" decoding="async" width="300" height="197" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Energy_diagram_for_enantioselective_synthesis.png/450px-Energy_diagram_for_enantioselective_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Energy_diagram_for_enantioselective_synthesis.png/600px-Energy_diagram_for_enantioselective_synthesis.png 2x" data-file-width="870" data-file-height="570" /></a><figcaption>An <a href="/wiki/Energy_profile_(chemistry)" title="Energy profile (chemistry)">energy profile</a> of an enantioselective addition reaction.</figcaption></figure> <p>Many of the building blocks of biological systems such as <a href="/wiki/Sugar" title="Sugar">sugars</a> and <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> are produced exclusively as one <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>. As a result, living systems possess a high degree of <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chemical chirality</a> and will often react differently with the various enantiomers of a given compound. Examples of this selectivity include: </p> <ul><li><b>Flavour:</b> the <a href="/wiki/Artificial_sweetener" class="mw-redirect" title="Artificial sweetener">artificial sweetener</a> <a href="/wiki/Aspartame" title="Aspartame">aspartame</a> has two enantiomers. <small>L</small>-aspartame tastes sweet whereas <small>D</small>-aspartame is tasteless.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><b>Odor:</b> <i>R</i>-(–)-<a href="/wiki/Carvone" title="Carvone">carvone</a> smells like <a href="/wiki/Spearmint" title="Spearmint">spearmint</a> whereas <i>S</i>-(+)-carvone smells like <a href="/wiki/Caraway" title="Caraway">caraway</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li><b>Drug effectiveness:</b> the <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> drug <a href="/wiki/Citalopram" title="Citalopram">Citalopram</a> is sold as a <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> mixture. However, studies have shown that only the (<i>S</i>)-(+) enantiomer is responsible for the drug's beneficial effects.<sup id="cite_ref-pmid15107657_5-0" class="reference"><a href="#cite_note-pmid15107657-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><b>Drug safety:</b> <a href="/wiki/Penicillamine" title="Penicillamine"><small>D</small>‑penicillamine</a> is used in <a href="/wiki/Chelation_therapy" title="Chelation therapy">chelation therapy</a> and for the treatment of <a href="/wiki/Rheumatoid_arthritis" title="Rheumatoid arthritis">rheumatoid arthritis</a> whereas <small>L</small>‑penicillamine is toxic as it inhibits the action of <a href="/wiki/Pyridoxine" title="Pyridoxine">pyridoxine</a>, an essential B vitamin.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li></ul> <p>As such enantioselective synthesis is of great importance but it can also be difficult to achieve. Enantiomers possess identical <a href="/wiki/Enthalpy_of_formation" class="mw-redirect" title="Enthalpy of formation">enthalpies</a> and <a href="/wiki/Entropy" title="Entropy">entropies</a> and hence should be produced in equal amounts by an undirected process – leading to a <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> mixture. Enantioselective synthesis can be achieved by using a chiral feature that favors the formation of one enantiomer over another through interactions at the <a href="/wiki/Transition_state" title="Transition state">transition state</a>. This biasing is known as <a href="/wiki/Asymmetric_induction" title="Asymmetric induction">asymmetric induction</a> and can involve chiral features in the <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrate</a>, <a href="/wiki/Reagent" title="Reagent">reagent</a>, <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, or environment<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and works by making the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> required to form one enantiomer lower than that of the opposing enantiomer.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Enantioselectivity is usually determined by the relative rates of an enantiodifferentiating step—the point at which one reactant can become either of two enantiomeric products. The <a href="/wiki/Rate_constant" class="mw-redirect" title="Rate constant">rate constant</a>, <i>k</i>, for a reaction is function of the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> of the reaction, sometimes called the <i>energy barrier</i>, and is temperature-dependent. Using the <a href="/wiki/Gibbs_free_energy" title="Gibbs free energy">Gibbs free energy</a> of the energy barrier, Δ<i>G</i>*, means that the relative rates for opposing stereochemical outcomes at a given temperature, <i>T</i>, is: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\frac {k_{1}}{k_{2}}}=10^{\frac {\Delta \Delta G^{*}}{T\times 1.98\times 2.3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <msub> <mi>k</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <msub> <mi>k</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mfrac> </mrow> <mo>=</mo> <msup> <mn>10</mn> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow> <mi mathvariant="normal">Δ</mi> <mi mathvariant="normal">Δ</mi> <msup> <mi>G</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>∗</mo> </mrow> </msup> </mrow> <mrow> <mi>T</mi> <mo>×</mo> <mn>1.98</mn> <mo>×</mo> <mn>2.3</mn> </mrow> </mfrac> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\frac {k_{1}}{k_{2}}}=10^{\frac {\Delta \Delta G^{*}}{T\times 1.98\times 2.3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/53c995b0d07d9b987a491bf556873edcfe394ce5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.338ex; width:16.688ex; height:5.843ex;" alt="{\displaystyle {\frac {k_{1}}{k_{2}}}=10^{\frac {\Delta \Delta G^{*}}{T\times 1.98\times 2.3}}}"></span></dd></dl> <p>This temperature dependence means the rate difference, and therefore the enantioselectivity, is greater at lower temperatures. As a result, even small energy-barrier differences can lead to a noticeable effect. </p> <dl><dd><table class="wikitable"> <tbody><tr> <th>ΔΔ<i>G</i>* (kcal) </th> <th colspan="2"><style data-mw-deduplicate="TemplateStyles:r1214402035">.mw-parser-output .sfrac{white-space:nowrap}.mw-parser-output .sfrac.tion,.mw-parser-output .sfrac .tion{display:inline-block;vertical-align:-0.5em;font-size:85%;text-align:center}.mw-parser-output .sfrac .num{display:block;line-height:1em;margin:0.0em 0.1em;border-bottom:1px solid}.mw-parser-output .sfrac .den{display:block;line-height:1em;margin:0.1em 0.1em}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="sfrac">⁠<span class="tion"><span class="num"><i>k</i><sub>1</sub></span><span class="sr-only">/</span><span class="den"><i>k</i><sub>2</sub></span></span>⁠</span> at 273 K </th> <th colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num"><i>k</i><sub>1</sub></span><span class="sr-only">/</span><span class="den"><i>k</i><sub>2</sub></span></span>⁠</span> at 298 K </th> <th colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num"><i>k</i><sub>1</sub></span><span class="sr-only">/</span><span class="den"><i>k</i><sub>2</sub></span></span>⁠</span> at 323 K) </th></tr> <tr> <td style="text-align:center;">1.0 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">6<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.37 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">5<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.46 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">4<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.78 </td></tr> <tr> <td style="text-align:center;">2.0 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">40<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.6 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">29<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.8 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">22<br /> </td> <td style="; text-align:left; border-left: none; padding-left: 0;">.9 </td></tr> <tr> <td style="text-align:center;">3.0 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">259 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">162 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">109 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td></tr> <tr> <td style="text-align:center;">4.0 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">1650 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">886 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">524 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td></tr> <tr> <td style="text-align:center;">5.0 </td> <td style="; text-align:right; border-right: none; padding-right: 0;">10500 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">4830 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td> <td style="; text-align:right; border-right: none; padding-right: 0;">2510 </td> <td style="; text-align:left; border-left: none; padding-left: 0;"> </td></tr></tbody></table></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Approaches">Approaches</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=2" title="Edit section: Approaches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Enantioselective_catalysis">Enantioselective catalysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=3" title="Edit section: Enantioselective catalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Enantioselective catalysis (known traditionally as "asymmetric catalysis") is performed using chiral <a href="/wiki/Catalysts" class="mw-redirect" title="Catalysts">catalysts</a>, which are typically chiral <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a>. Catalysis is effective for a broader range of transformations than any other method of enantioselective synthesis. The chiral metal catalysts are almost invariably rendered chiral by using <a href="/wiki/Chiral_ligand" class="mw-redirect" title="Chiral ligand">chiral ligands</a>, but it is possible to generate chiral-at-metal complexes composed entirely of <a href="/wiki/Achiral" class="mw-redirect" title="Achiral">achiral</a> ligands.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Most enantioselective catalysts are effective at low substrate/catalyst ratios.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Given their high efficiencies, they are often suitable for industrial scale synthesis, even with expensive catalysts.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> A versatile example of enantioselective synthesis is <a href="/wiki/Asymmetric_hydrogenation" title="Asymmetric hydrogenation">asymmetric hydrogenation</a>, which is used to reduce a wide variety of <a href="/wiki/Functional_group" title="Functional group">functional groups</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Noyori_Asymmetric_Hydrogenation_Scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Noyori_Asymmetric_Hydrogenation_Scheme.png/400px-Noyori_Asymmetric_Hydrogenation_Scheme.png" decoding="async" width="400" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Noyori_Asymmetric_Hydrogenation_Scheme.png/600px-Noyori_Asymmetric_Hydrogenation_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Noyori_Asymmetric_Hydrogenation_Scheme.png/800px-Noyori_Asymmetric_Hydrogenation_Scheme.png 2x" data-file-width="1617" data-file-height="244" /></a><figcaption></figcaption></figure> <p>The design of new catalysts is dominated by the development of new classes of <a href="/wiki/Ligand" title="Ligand">ligands</a>. Certain ligands, often referred to as "<a href="/wiki/Privileged_ligand" class="mw-redirect" title="Privileged ligand">privileged ligands</a>", are effective in a wide range of reactions; examples include <a href="/wiki/BINOL" class="mw-redirect" title="BINOL">BINOL</a>, <a href="/wiki/Salen_ligand" title="Salen ligand">Salen</a>, and <a href="/wiki/Bisoxazoline_ligand" title="Bisoxazoline ligand">BOX</a>. Most catalysts are effective for only one type of asymmetric reaction. For example, <a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a> with BINAP/Ru requires a β-ketone, although another catalyst, BINAP/diamine-Ru, widens the scope to α,β-<a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a> and <a href="/wiki/Aromatic_chemical" class="mw-redirect" title="Aromatic chemical">aromatic chemicals</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Chiral_auxiliaries">Chiral auxiliaries</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=4" title="Edit section: Chiral auxiliaries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Chiral_auxiliary" title="Chiral auxiliary">Chiral auxiliary</a></div> <p>A chiral auxiliary is an organic compound which couples to the starting material to form a new compound which can then undergo diastereoselective reactions via intramolecular asymmetric induction.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Glorius_review_18-0" class="reference"><a href="#cite_note-Glorius_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> At the end of the reaction the auxiliary is removed, under conditions that will not cause <a href="/wiki/Racemization" title="Racemization">racemization</a> of the product.<sup id="cite_ref-Evans_review_19-0" class="reference"><a href="#cite_note-Evans_review-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It is typically then recovered for future use. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Auxiliary_general_scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Auxiliary_general_scheme.png/500px-Auxiliary_general_scheme.png" decoding="async" width="500" height="177" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Auxiliary_general_scheme.png/750px-Auxiliary_general_scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Auxiliary_general_scheme.png/1000px-Auxiliary_general_scheme.png 2x" data-file-width="1759" data-file-height="623" /></a><figcaption></figcaption></figure> <p>Chiral auxiliaries must be used in <a href="/wiki/Stoichiometric" class="mw-redirect" title="Stoichiometric">stoichiometric</a> amounts to be effective and require additional synthetic steps to append and remove the auxiliary. However, in some cases the only available stereoselective methodology relies on chiral auxiliaries and these reactions tend to be versatile and very well-studied, allowing the most time-efficient access to enantiomerically pure products.<sup id="cite_ref-Glorius_review_18-1" class="reference"><a href="#cite_note-Glorius_review-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Additionally, the products of auxiliary-directed reactions are <a href="/wiki/Diastereomers" class="mw-redirect" title="Diastereomers">diastereomers</a>, which enables their facile separation by methods such as <a href="/wiki/Column_chromatography" title="Column chromatography">column chromatography</a> or crystallization. </p> <div class="mw-heading mw-heading3"><h3 id="Biocatalysis">Biocatalysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=5" title="Edit section: Biocatalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Biocatalysis" title="Biocatalysis">Biocatalysis</a></div> <p>Biocatalysis makes use of biological compounds, ranging from isolated <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> to living cells, to perform chemical transformations.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The advantages of these reagents include very high <a href="/wiki/Enantiomeric_excess" title="Enantiomeric excess">e.e.s</a> and reagent specificity, as well as mild operating conditions and <a href="/wiki/Green_chemistry" title="Green chemistry">low environmental impact</a>. Biocatalysts are more commonly used in industry than in academic research;<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> for example in the production of <a href="/wiki/Statin" title="Statin">statins</a>.<sup id="cite_ref-statin_23-0" class="reference"><a href="#cite_note-statin-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The high reagent specificity can be a problem, however, as it often requires that a wide range of biocatalysts be screened before an effective reagent is found. </p> <div class="mw-heading mw-heading3"><h3 id="Enantioselective_organocatalysis">Enantioselective organocatalysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=6" title="Edit section: Enantioselective organocatalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Organocatalysis" title="Organocatalysis">Organocatalysis</a></div> <p>Organocatalysis refers to a form of <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>, where the rate of a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> is increased by an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> consisting of <a href="/wiki/Carbon" title="Carbon">carbon</a>, <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> and other non-metal elements.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Special_Issue_Chem_Rev_25-0" class="reference"><a href="#cite_note-Special_Issue_Chem_Rev-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> When the organocatalyst is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>, then enantioselective synthesis can be achieved;<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> for example a number of carbon–carbon bond forming reactions become enantioselective in the presence of <a href="/wiki/Proline" title="Proline">proline</a> with the <a href="/wiki/Aldol_reaction#Organocatalysis" title="Aldol reaction">aldol reaction</a> being a prime example.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Organocatalysis often employs natural compounds and <a href="/wiki/Secondary_amine" class="mw-redirect" title="Secondary amine">secondary amines</a> as chiral catalysts;<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> these are inexpensive and <a href="/wiki/Green_chemistry" title="Green chemistry">environmentally friendly</a>, as no metals are involved. </p> <div class="mw-heading mw-heading3"><h3 id="Chiral_pool_synthesis">Chiral pool synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=7" title="Edit section: Chiral pool synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Chiral_pool_synthesis" class="mw-redirect" title="Chiral pool synthesis">Chiral pool synthesis</a></div> <p>Chiral pool synthesis is one of the simplest and oldest approaches for enantioselective synthesis. A readily available chiral starting material is manipulated through successive reactions, often using achiral reagents, to obtain the desired target molecule. This can meet the criteria for enantioselective synthesis when a new chiral species is created, such as in an <a href="/wiki/SN2_reaction" title="SN2 reaction">S<sub>N</sub>2 reaction</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:SN2_reaction_mechanism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/SN2_reaction_mechanism.png/450px-SN2_reaction_mechanism.png" decoding="async" width="450" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/SN2_reaction_mechanism.png/675px-SN2_reaction_mechanism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/39/SN2_reaction_mechanism.png/900px-SN2_reaction_mechanism.png 2x" data-file-width="1487" data-file-height="261" /></a><figcaption></figcaption></figure> <p>Chiral pool synthesis is especially attractive for target molecules having similar chirality to a relatively inexpensive naturally occurring building-block such as a sugar or <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>. However, the number of possible reactions the molecule can undergo is restricted and tortuous synthetic routes may be required (e.g. <a href="/wiki/Oseltamivir_total_synthesis" title="Oseltamivir total synthesis">Oseltamivir total synthesis</a>). This approach also requires a <a href="/wiki/Stoichiometric" class="mw-redirect" title="Stoichiometric">stoichiometric</a> amount of the <a href="/wiki/Enantiopure" class="mw-redirect" title="Enantiopure">enantiopure</a> starting material, which can be expensive if it is not naturally occurring. </p> <div class="mw-heading mw-heading2"><h2 id="Separation_and_analysis_of_enantiomers">Separation and analysis of enantiomers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=8" title="Edit section: Separation and analysis of enantiomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The two enantiomers of a molecule possess many of the same physical properties (e.g. <a href="/wiki/Melting_point" title="Melting point">melting point</a>, <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a>, <a href="/wiki/Chemical_polarity" title="Chemical polarity">polarity</a> etc.) and so behave identically to each other. As a result, they will migrate with an identical R<sub>f</sub> in <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">thin layer chromatography</a> and have identical retention times in <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a> and <a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a>. Their <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> and <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a> spectra are identical. </p><p>This can make it very difficult to determine whether a process has produced a single enantiomer (and crucially which enantiomer it is) as well as making it hard to separate enantiomers from a reaction which has not been 100% enantioselective. Fortunately, enantiomers behave differently in the presence of other chiral materials and this can be exploited to allow their separation and analysis. </p><p>Enantiomers do not migrate identically on chiral chromatographic media, such as <a href="/wiki/Quartz" title="Quartz">quartz</a> or standard media that has been chirally modified. This forms the basis of <a href="/wiki/Chiral_column_chromatography" title="Chiral column chromatography">chiral column chromatography</a>, which can be used on a small scale to allow analysis via <a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a> and <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a>, or on a large scale to separate chirally impure materials. However this process can require large amount of chiral packing material which can be expensive. A common alternative is to use a <a href="/wiki/Chiral_derivatizing_agent" title="Chiral derivatizing agent">chiral derivatizing agent</a> to convert the enantiomers into a diastereomers, in much the same way as chiral auxiliaries. These have different physical properties and hence can be separated and analysed using conventional methods. Special chiral derivitizing agents known as 'chiral resolution agents' are used in the <a href="/wiki/NMR_spectroscopy_of_stereoisomers" class="mw-redirect" title="NMR spectroscopy of stereoisomers">NMR spectroscopy of stereoisomers</a>, these typically involve coordination to chiral <a href="/wiki/Europium" title="Europium">europium</a> complexes such as <a href="/wiki/EuFOD" title="EuFOD">Eu(fod)<sub>3</sub></a> and Eu(hfc)<sub>3</sub>. </p><p>The separation and analysis of component enantiomers of a racemic drugs or pharmaceutical substances are referred to as <a href="/wiki/Chiral_analysis" title="Chiral analysis">chiral analysis</a>.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Enantioselective_analysis" class="mw-redirect" title="Enantioselective analysis">enantioselective analysis</a>. The most frequently employed technique to carry out chiral analysis involves separation science procedures, specifically chiral chromatographic methods.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Enantiomeric_excess" title="Enantiomeric excess">enantiomeric excess</a> of a substance can also be determined using certain optical methods. The oldest method for doing this is to use a <a href="/wiki/Polarimeter" title="Polarimeter">polarimeter</a> to compare the level of <a href="/wiki/Optical_rotation" title="Optical rotation">optical rotation</a> in the product against a 'standard' of known composition. It is also possible to perform <a href="/wiki/Ultraviolet-visible_spectroscopy_of_stereoisomers" class="mw-redirect" title="Ultraviolet-visible spectroscopy of stereoisomers">ultraviolet-visible spectroscopy of stereoisomers</a> by exploiting the <a href="/wiki/Cotton_effect" title="Cotton effect">Cotton effect</a>. </p><p>One of the most accurate ways of determining the chirality of compound is to determine its <a href="/wiki/Absolute_configuration" title="Absolute configuration">absolute configuration</a> by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>. However this is a labour-intensive process which requires that a suitable <a href="/wiki/Single_crystal" title="Single crystal">single crystal</a> be grown. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Inception_(1815–1905)"><span id="Inception_.281815.E2.80.931905.29"></span>Inception (1815–1905)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=10" title="Edit section: Inception (1815–1905)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1815 the French physicist <a href="/wiki/Jean-Baptiste_Biot" title="Jean-Baptiste Biot">Jean-Baptiste Biot</a> showed that certain chemicals could rotate the plane of a beam of polarised light, a property called <a href="/wiki/Optical_activity" class="mw-redirect" title="Optical activity">optical activity</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The nature of this property remained a mystery until 1848, when <a href="/wiki/Louis_Pasteur" title="Louis Pasteur">Louis Pasteur</a> proposed that it had a molecular basis originating from some form of <i>dissymmetry</i>,<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> with the term <i>chirality</i> being coined by <a href="/wiki/Lord_Kelvin" title="Lord Kelvin">Lord Kelvin</a> a year later.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> The origin of chirality itself was finally described in 1874, when <a href="/wiki/Jacobus_Henricus_van_%27t_Hoff" title="Jacobus Henricus van 't Hoff">Jacobus Henricus van 't Hoff</a> and <a href="/wiki/Joseph_Le_Bel" class="mw-redirect" title="Joseph Le Bel">Joseph Le Bel</a> independently proposed the <a href="/wiki/Tetrahedral" class="mw-redirect" title="Tetrahedral">tetrahedral</a> geometry of carbon.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Structural models prior to this work had been two-dimensional, and van 't Hoff and Le Bel theorized that the arrangement of groups around this tetrahedron could dictate the optical activity of the resulting compound through what became known as the <a href="/wiki/Le_Bel%E2%80%93van_%27t_Hoff_rule" class="mw-redirect" title="Le Bel–van 't Hoff rule">Le Bel–van 't Hoff rule</a>. </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:MarckwaldAsymmetricSynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/MarckwaldAsymmetricSynthesis.svg/600px-MarckwaldAsymmetricSynthesis.svg.png" decoding="async" width="600" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/MarckwaldAsymmetricSynthesis.svg/900px-MarckwaldAsymmetricSynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/MarckwaldAsymmetricSynthesis.svg/1200px-MarckwaldAsymmetricSynthesis.svg.png 2x" data-file-width="484" data-file-height="83" /></a><figcaption>Marckwald's brucine-catalyzed enantioselective decarboxylation of 2-ethyl-2-methyl<a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a>, resulting in a slight excess of the <a href="/wiki/Levorotary" class="mw-redirect" title="Levorotary">levorotary</a> form of the 2-methylbutyric acid product.<sup id="cite_ref-Koskinen2012_38-0" class="reference"><a href="#cite_note-Koskinen2012-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>In 1894 <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Hermann Emil Fischer</a> outlined the concept of <a href="/wiki/Asymmetric_induction" title="Asymmetric induction">asymmetric induction</a>;<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> in which he correctly ascribed selective the formation of <small>D</small>-glucose by plants to be due to the influence of optically active substances within chlorophyll. Fischer also successfully performed what would now be regarded as the first example of enantioselective synthesis, by enantioselectively elongating sugars via a process which would eventually become the <a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Brucine2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Brucine2.svg/200px-Brucine2.svg.png" decoding="async" width="200" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Brucine2.svg/300px-Brucine2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Brucine2.svg/400px-Brucine2.svg.png 2x" data-file-width="440" data-file-height="289" /></a><figcaption>Brucine, an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> <a href="/wiki/Natural_product" title="Natural product">natural product</a> related to <a href="/wiki/Strychnine" title="Strychnine">strychnine</a>, used successfully as an <a href="/wiki/Organocatalyst" class="mw-redirect" title="Organocatalyst">organocatalyst</a> by Marckwald in 1904.<sup id="cite_ref-Koskinen2012_38-1" class="reference"><a href="#cite_note-Koskinen2012-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The first enantioselective chemical synthesis is most often attributed to <a href="/wiki/Willy_Marckwald" title="Willy Marckwald">Willy Marckwald</a>, <a href="/wiki/Humboldt-Universit%C3%A4t_zu_Berlin" class="mw-redirect" title="Humboldt-Universität zu Berlin">Universität zu Berlin</a>, for a <a href="/wiki/Brucine" title="Brucine">brucine</a>-catalyzed enantioselective <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of 2-ethyl-2-methyl<a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a> reported in 1904.<sup id="cite_ref-Koskinen2012_38-2" class="reference"><a href="#cite_note-Koskinen2012-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> A slight excess of the levorotary form of the product of the reaction, 2-methylbutyric acid, was produced; as this product is also a <a href="/wiki/Natural_product" title="Natural product">natural product</a>—e.g., as a side chain of <a href="/wiki/Lovastatin" title="Lovastatin">lovastatin</a> formed by its diketide synthase (LovF) during its <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup>—this result constitutes the first recorded total synthesis with enantioselectivity, as well other firsts (as Koskinen notes, first "example of <a href="/wiki/Asymmetric_catalysis" class="mw-redirect" title="Asymmetric catalysis">asymmetric catalysis</a>, <a href="/wiki/Enantioselectivity" class="mw-redirect" title="Enantioselectivity">enantiotopic selection</a>, and <a href="/wiki/Organocatalysis" title="Organocatalysis">organocatalysis</a>").<sup id="cite_ref-Koskinen2012_38-3" class="reference"><a href="#cite_note-Koskinen2012-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> This observation is also of historical significance, as at the time enantioselective synthesis could only be understood in terms of <a href="/wiki/Vitalism" title="Vitalism">vitalism</a>. At the time many prominent chemists such as <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> argued that natural and artificial compounds were fundamentally different and that chirality was simply a manifestation of the 'vital force' which could only exist in natural compounds.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Unlike Fischer, Marckwald had performed an enantioselective reaction upon an achiral, <i>un-natural</i> starting material, albeit with a chiral organocatalyst (as we now understand this chemistry).<sup id="cite_ref-Koskinen2012_38-4" class="reference"><a href="#cite_note-Koskinen2012-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Early_work_(1905–1965)"><span id="Early_work_.281905.E2.80.931965.29"></span>Early work (1905–1965)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=11" title="Edit section: Early work (1905–1965)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The development of enantioselective synthesis was initially slow, largely due to the limited range of techniques available for their separation and analysis. Diastereomers possess different physical properties, allowing separation by conventional means, however at the time enantiomers could only be separated by <a href="/wiki/Spontaneous_resolution" class="mw-redirect" title="Spontaneous resolution">spontaneous resolution</a> (where enantiomers separate upon crystallisation) or <a href="/wiki/Kinetic_resolution" title="Kinetic resolution">kinetic resolution</a> (where one enantiomer is selectively destroyed). The only tool for analysing enantiomers was <a href="/wiki/Optical_activity" class="mw-redirect" title="Optical activity">optical activity</a> using a <a href="/wiki/Polarimeter" title="Polarimeter">polarimeter</a>, a method which provides no structural data. </p><p>It was not until the 1950s that major progress really began. Driven in part by chemists such as <a href="/wiki/R._B._Woodward" class="mw-redirect" title="R. B. Woodward">R. B. Woodward</a> and <a href="/wiki/Vladimir_Prelog" title="Vladimir Prelog">Vladimir Prelog</a> but also by the development of new techniques. The first of these was <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>, which was used to determine the <a href="/wiki/Absolute_configuration" title="Absolute configuration">absolute configuration</a> of an organic compound by <a href="/wiki/Johannes_Martin_Bijvoet" title="Johannes Martin Bijvoet">Johannes Bijvoet</a> in 1951.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Chiral chromatography was introduced a year later by Dalgliesh, who used <a href="/wiki/Paper_chromatography" title="Paper chromatography">paper chromatography</a> to separate chiral amino acids.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Although Dalgliesh was not the first to observe such separations, he correctly attributed the separation of enantiomers to differential retention by the chiral cellulose. This was expanded upon in 1960, when Klem and Reed first reported the use of chirally-modified silica gel for chiral <a href="/wiki/HPLC" class="mw-redirect" title="HPLC">HPLC</a> separation.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thalidomide-structures.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Thalidomide-structures.png/300px-Thalidomide-structures.png" decoding="async" width="300" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Thalidomide-structures.png/450px-Thalidomide-structures.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Thalidomide-structures.png/600px-Thalidomide-structures.png 2x" data-file-width="1100" data-file-height="594" /></a><figcaption>The two enantiomers of thalidomide:<br />Left: (<i>S</i>)-thalidomide<br />Right: (<i>R</i>)-thalidomide</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Thalidomide">Thalidomide</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=12" title="Edit section: Thalidomide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While it was known that the different enantiomers of a drug could have different activities, with significant early work being done by <a href="/wiki/Arthur_Robertson_Cushny" title="Arthur Robertson Cushny">Arthur Robertson Cushny</a>,<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> this was not accounted for in early drug design and testing. However, following the <a href="/wiki/Thalidomide" title="Thalidomide">thalidomide</a> disaster the development and licensing of drugs changed dramatically. </p><p>First synthesized in 1953, thalidomide was widely prescribed for morning sickness from 1957 to 1962, but was soon found to be seriously <a href="/wiki/Teratogenic" class="mw-redirect" title="Teratogenic">teratogenic</a>,<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> eventually causing birth defects in more than 10,000 babies. The disaster prompted many countries to introduce tougher rules for the testing and licensing of drugs, such as the <a href="/wiki/Kefauver-Harris_Amendment" class="mw-redirect" title="Kefauver-Harris Amendment">Kefauver-Harris Amendment</a> (US) and <a href="/wiki/Directive_65/65/EEC1" class="mw-redirect" title="Directive 65/65/EEC1">Directive 65/65/EEC1</a> (EU). </p><p>Early research into the teratogenic mechanism, using mice, suggested that one enantiomer of thalidomide was teratogenic while the other possessed all the therapeutic activity. This theory was later shown to be incorrect and has now been superseded by a body of research.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> However it raised the importance of chirality in drug design, leading to increased research into enantioselective synthesis. </p> <div class="mw-heading mw-heading3"><h3 id="Modern_age_(since_1965)"><span id="Modern_age_.28since_1965.29"></span>Modern age (since 1965)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=13" title="Edit section: Modern age (since 1965)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Cahn–Ingold–Prelog priority rules (often abbreviated as the <a href="/wiki/CIP_system" class="mw-redirect" title="CIP system">CIP system</a>) were first published in 1966; allowing enantiomers to be more easily and accurately described.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> The same year saw first successful enantiomeric separation by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> an important development as the technology was in common use at the time. </p><p>Metal-catalysed enantioselective synthesis was pioneered by <a href="/wiki/William_S._Knowles" class="mw-redirect" title="William S. Knowles">William S. Knowles</a>, <a href="/wiki/Ry%C5%8Dji_Noyori" title="Ryōji Noyori">Ryōji Noyori</a> and <a href="/wiki/K._Barry_Sharpless" class="mw-redirect" title="K. Barry Sharpless">K. Barry Sharpless</a>; for which they would receive the 2001 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a>. Knowles and Noyori began with the development of <a href="/wiki/Asymmetric_hydrogenation" title="Asymmetric hydrogenation">asymmetric hydrogenation</a>, which they developed independently in 1968. Knowles replaced the achiral <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a> ligands in <a href="/wiki/Wilkinson%27s_catalyst" title="Wilkinson's catalyst">Wilkinson's catalyst</a> with chiral <a href="/wiki/Phosphine_ligand" class="mw-redirect" title="Phosphine ligand">phosphine ligands</a>. This experimental catalyst was employed in an asymmetric hydrogenation with a modest 15% <a href="/wiki/Enantiomeric_excess" title="Enantiomeric excess">enantiomeric excess</a>. Knowles was also the first to apply enantioselective metal catalysis to industrial-scale synthesis; while working for the <a href="/wiki/Monsanto_Company" class="mw-redirect" title="Monsanto Company">Monsanto Company</a> he developed an enantioselective hydrogenation step for the production of <a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a>, utilising the <a href="/wiki/DIPAMP" title="DIPAMP">DIPAMP</a> ligand.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <table align="center"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Hydrogenation-Knowles1968.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Hydrogenation-Knowles1968.png/350px-Hydrogenation-Knowles1968.png" decoding="async" width="350" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Hydrogenation-Knowles1968.png/525px-Hydrogenation-Knowles1968.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Hydrogenation-Knowles1968.png/700px-Hydrogenation-Knowles1968.png 2x" data-file-width="1073" data-file-height="435" /></a></span> </td> <td width="100px"> </td> <td><span typeof="mw:File"><a href="/wiki/File:AsymmetricSynthesisNoyori.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/AsymmetricSynthesisNoyori.png/350px-AsymmetricSynthesisNoyori.png" decoding="async" width="350" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/AsymmetricSynthesisNoyori.png/525px-AsymmetricSynthesisNoyori.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/AsymmetricSynthesisNoyori.png/700px-AsymmetricSynthesisNoyori.png 2x" data-file-width="1056" data-file-height="748" /></a></span> </td></tr> <tr> <th align="center">Knowles: Asymmetric hydrogenation (1968) </th> <td width="100px"> </td> <th align="center">Noyori: Enantioselective cyclopropanation (1968) </th></tr></tbody></table> <p>Noyori devised a copper complex using a chiral <a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a> ligand, which he used for the <a href="/wiki/Intermolecular_metal-catalyzed_carbenoid_cyclopropanations" class="mw-redirect" title="Intermolecular metal-catalyzed carbenoid cyclopropanations">metal–carbenoid cyclopropanation</a> of <a href="/wiki/Styrene" title="Styrene">styrene</a>.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> In common with Knowles' findings, Noyori's results for the enantiomeric excess for this first-generation ligand were disappointingly low: 6%. However continued research eventually led to the development of the <a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a> reaction. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Sharpless_Oxyamination_Scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Sharpless_Oxyamination_Scheme.png/250px-Sharpless_Oxyamination_Scheme.png" decoding="async" width="250" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Sharpless_Oxyamination_Scheme.png/375px-Sharpless_Oxyamination_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Sharpless_Oxyamination_Scheme.png/500px-Sharpless_Oxyamination_Scheme.png 2x" data-file-width="979" data-file-height="202" /></a><figcaption>The Sharpless oxyamination</figcaption></figure> <p>Sharpless complemented these reduction reactions by developing a range of asymmetric oxidations (<a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a>,<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Sharpless_asymmetric_dihydroxylation" title="Sharpless asymmetric dihydroxylation">Sharpless asymmetric dihydroxylation</a>,<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Sharpless_oxyamination" title="Sharpless oxyamination">Sharpless oxyamination</a><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup>) during the 1970s and 1980s. With the asymmetric oxyamination reaction, using <a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">osmium tetroxide</a>, being the earliest. </p><p>During the same period, methods were developed to allow the analysis of chiral compounds by <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a>; either using chiral derivatizing agents, such as <a href="/wiki/Mosher%27s_acid" title="Mosher's acid">Mosher's acid</a>,<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Europium" title="Europium">europium</a> based shift reagents, of which Eu(DPM)<sub>3</sub> was the earliest.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>Chiral auxiliaries were introduced by <a href="/wiki/E.J._Corey" class="mw-redirect" title="E.J. Corey">E.J. Corey</a> in 1978<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> and featured prominently in the work of <a href="/wiki/Dieter_Enders" title="Dieter Enders">Dieter Enders</a>. Around the same time enantioselective organocatalysis was developed, with pioneering work including the <a href="/wiki/Hajos%E2%80%93Parrish%E2%80%93Eder%E2%80%93Sauer%E2%80%93Wiechert_reaction" class="mw-redirect" title="Hajos–Parrish–Eder–Sauer–Wiechert reaction">Hajos–Parrish–Eder–Sauer–Wiechert reaction</a>. Enzyme-catalyzed enantioselective reactions became more and more common during the 1980s,<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> particularly in industry,<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> with their applications including <a href="/wiki/Asymmetric_ester_hydrolysis_with_pig-liver_esterase" title="Asymmetric ester hydrolysis with pig-liver esterase">asymmetric ester hydrolysis with pig-liver esterase</a>. The emerging technology of <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetic engineering</a> has allowed the tailoring of enzymes to specific processes, permitting an increased range of selective transformations. For example, in the asymmetric hydrogenation of <a href="/wiki/Statin" title="Statin">statin</a> precursors.<sup id="cite_ref-statin_23-1" class="reference"><a href="#cite_note-statin-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a>, for the use of a chiral ionic liquid in enantioselective synthesis</li> <li><a href="/wiki/Kelliphite" title="Kelliphite">Kelliphite</a>, a chiral ligand widely used in asymmetric synthesis</li> <li><a href="/wiki/Spontaneous_absolute_asymmetric_synthesis" title="Spontaneous absolute asymmetric synthesis">Spontaneous absolute asymmetric synthesis</a>, the synthesis of chiral products from achiral precursors and without the use of optically active catalysts or auxiliaries. It is relevant to the discussion <a href="/wiki/Homochirality" title="Homochirality">homochirality</a> in nature.</li> <li><a href="/wiki/Tacticity" title="Tacticity">Tacticity</a>, a property of <a href="/wiki/Polymer" title="Polymer">polymers</a> which originates from enantioselective synthesis</li> <li><a href="/wiki/Chiral_analysis" title="Chiral analysis">Chiral analysis</a></li> <li><a href="/wiki/Enantioselective_analysis" class="mw-redirect" title="Enantioselective analysis">Enantioselective analysis</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantioselective_synthesis&action=edit&section=15" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. 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II"</a>. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>22</b> (1): 365–376. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18890220183">10.1002/cber.18890220183</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+Mannose.+II&rft.volume=22&rft.issue=1&rft.pages=365-376&rft.date=1889-01-01&rft_id=info%3Adoi%2F10.1002%2Fcber.18890220183&rft.aulast=Fischer&rft.aufirst=Emil&rft.au=Hirschberger%2C+Josef&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425553&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarckwald,_W.1904" class="citation journal cs1">Marckwald, W. (1904). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426100">"Ueber asymmetrische Synthese"</a>. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>37</b>: 349–354. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19040370165">10.1002/cber.19040370165</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+asymmetrische+Synthese&rft.volume=37&rft.pages=349-354&rft.date=1904&rft_id=info%3Adoi%2F10.1002%2Fcber.19040370165&rft.au=Marckwald%2C+W.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426100&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCampbellVederas2010" class="citation journal cs1">Campbell, Chantel D.; Vederas, John C. (23 June 2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fbip.21428">"Biosynthesis of lovastatin and related metabolites formed by fungal iterative PKS enzymes"</a>. <i>Biopolymers</i>. <b>93</b> (9): 755–763. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fbip.21428">10.1002/bip.21428</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20577995">20577995</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biopolymers&rft.atitle=Biosynthesis+of+lovastatin+and+related+metabolites+formed+by+fungal+iterative+PKS+enzymes&rft.volume=93&rft.issue=9&rft.pages=755-763&rft.date=2010-06-23&rft_id=info%3Adoi%2F10.1002%2Fbip.21428&rft_id=info%3Apmid%2F20577995&rft.aulast=Campbell&rft.aufirst=Chantel+D.&rft.au=Vederas%2C+John+C.&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fbip.21428&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCornish-Bawden1997" class="citation cs2">Cornish-Bawden, Athel, ed. (1997), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HFrBP8S7my4C&q=Berzelius+vitalism+1815&pg=PA73"><i>New Beer in an Old Bottle. Eduard Buchner and the Growth of Biochemical Knowledge</i></a>, Universitat de València, pp. 72–73, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-84-370-3328-0" title="Special:BookSources/978-84-370-3328-0"><bdi>978-84-370-3328-0</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=New+Beer+in+an+Old+Bottle.+Eduard+Buchner+and+the+Growth+of+Biochemical+Knowledge&rft.pages=72-73&rft.pub=Universitat+de+Val%C3%A8ncia&rft.date=1997&rft.isbn=978-84-370-3328-0&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHFrBP8S7my4C%26q%3DBerzelius%2Bvitalism%2B1815%26pg%3DPA73&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text">Much of this early work was published in German, however contemporary English accounts can be found in the papers of <a href="/wiki/Alexander_McKenzie_(chemist)" title="Alexander McKenzie (chemist)">Alexander McKenzie</a>, with continuing analysis and commentary in modern reviews such as Koskinen (2012).</span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcKenzie1904" class="citation journal cs1">McKenzie, Alexander (1 January 1904). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1567059">"CXXVII.Studies in asymmetric synthesis. I. Reduction of menthyl benzoylformate. II. Action of magnesium alkyl haloids on menthyl benzoylformate"</a>. <i>J. Chem. Soc. Trans</i>. <b>85</b>: 1249–1262. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FCT9048501249">10.1039/CT9048501249</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.+Trans.&rft.atitle=CXXVII.Studies+in+asymmetric+synthesis.+I.+Reduction+of+menthyl+benzoylformate.+II.+Action+of+magnesium+alkyl+haloids+on+menthyl+benzoylformate&rft.volume=85&rft.pages=1249-1262&rft.date=1904-01-01&rft_id=info%3Adoi%2F10.1039%2FCT9048501249&rft.aulast=McKenzie&rft.aufirst=Alexander&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1567059&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBijvoetPeerdeman,_A._F.van_Bommel,_A._J.1951" class="citation journal cs1">Bijvoet, J. M.; Peerdeman, A. F.; van Bommel, A. J. (1951). "Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays". <i>Nature</i>. <b>168</b> (4268): 271–272. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1951Natur.168..271B">1951Natur.168..271B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F168271a0">10.1038/168271a0</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4264310">4264310</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Determination+of+the+Absolute+Configuration+of+Optically+Active+Compounds+by+Means+of+X-Rays&rft.volume=168&rft.issue=4268&rft.pages=271-272&rft.date=1951&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4264310%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1038%2F168271a0&rft_id=info%3Abibcode%2F1951Natur.168..271B&rft.aulast=Bijvoet&rft.aufirst=J.+M.&rft.au=Peerdeman%2C+A.+F.&rft.au=van+Bommel%2C+A.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDalgliesh1952" class="citation journal cs1">Dalgliesh, C. E. (1952). "756. The optical resolution of aromatic amino-acids on paper chromatograms". <i>Journal of the Chemical Society (Resumed)</i>: 3940. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FJR9520003940">10.1039/JR9520003940</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society+%28Resumed%29&rft.atitle=756.+The+optical+resolution+of+aromatic+amino-acids+on+paper+chromatograms&rft.pages=3940&rft.date=1952&rft_id=info%3Adoi%2F10.1039%2FJR9520003940&rft.aulast=Dalgliesh&rft.aufirst=C.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKlemmReed,_David1960" class="citation journal cs1">Klemm, L.H.; Reed, David (1960). "Optical resolution by molecular complexation chromatography". <i>Journal of Chromatography A</i>. <b>3</b>: 364–368. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9673%2801%2997011-6">10.1016/S0021-9673(01)97011-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chromatography+A&rft.atitle=Optical+resolution+by+molecular+complexation+chromatography&rft.volume=3&rft.pages=364-368&rft.date=1960&rft_id=info%3Adoi%2F10.1016%2FS0021-9673%2801%2997011-6&rft.aulast=Klemm&rft.aufirst=L.H.&rft.au=Reed%2C+David&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCushny1903" class="citation journal cs1">Cushny, AR (2 November 1903). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1540678">"Atropine and the hyoscyamines-a study of the action of optical isomers"</a>. <i>The Journal of Physiology</i>. <b>30</b> (2): 176–94. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.1903.sp000988">10.1113/jphysiol.1903.sp000988</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1540678">1540678</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16992694">16992694</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=Atropine+and+the+hyoscyamines-a+study+of+the+action+of+optical+isomers&rft.volume=30&rft.issue=2&rft.pages=176-94&rft.date=1903-11-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1540678%23id-name%3DPMC&rft_id=info%3Apmid%2F16992694&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.1903.sp000988&rft.aulast=Cushny&rft.aufirst=AR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1540678&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-50">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCushnyPeebles,_AR1905" class="citation journal cs1">Cushny, AR; Peebles, AR (13 July 1905). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1465734">"The action of optical isomers: II. 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"Industrial Biocatalysis: Past, Present, and Future". <i>Organic Process Research & Development</i>. <b>4</b> (4): 286–290. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fop990101l">10.1021/op990101l</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Process+Research+%26+Development&rft.atitle=Industrial+Biocatalysis%3A+Past%2C+Present%2C+and+Future&rft.volume=4&rft.issue=4&rft.pages=286-290&rft.date=2000&rft_id=info%3Adoi%2F10.1021%2Fop990101l&rft.aulast=Wandrey&rft.aufirst=Christian&rft.au=Liese%2C+Andreas&rft.au=Kihumbu%2C+David&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnantioselective+synthesis" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist 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style="padding:0 0.25em"> <ul><li><a href="/wiki/Artificial_gene_synthesis" title="Artificial gene synthesis">Artificial gene synthesis</a></li> <li><a href="/wiki/Biomimetic_synthesis" title="Biomimetic synthesis">Biomimetic synthesis</a></li> <li><a href="/wiki/Bioretrosynthesis" title="Bioretrosynthesis">Bioretrosynthesis</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li> <li><a href="/wiki/Chemosynthesis_(nanotechnology)" title="Chemosynthesis (nanotechnology)">Chemosynthesis</a></li> <li><a href="/wiki/Convergent_synthesis" title="Convergent synthesis">Convergent synthesis</a></li> <li><a href="/wiki/Custom_peptide_synthesis" title="Custom peptide synthesis">Custom peptide synthesis</a></li> <li><a href="/wiki/Direct_process" title="Direct process">Direct process</a></li> <li><a href="/wiki/Divergent_synthesis" title="Divergent synthesis">Divergent synthesis</a></li> <li><a href="/wiki/Electrosynthesis" title="Electrosynthesis">Electrosynthesis</a></li> <li><a class="mw-selflink selflink">Enantioselective synthesis</a></li> <li><a href="/wiki/Fully_automated_synthesis" class="mw-redirect" title="Fully automated synthesis">Fully automated synthesis</a></li> <li><a href="/wiki/Hydrothermal_synthesis" title="Hydrothermal synthesis">Hydrothermal synthesis</a></li> <li><a href="/wiki/Laser_ablation_synthesis_in_solution" title="Laser ablation synthesis in solution">LASiS</a></li> <li><a href="/wiki/Mechanosynthesis" title="Mechanosynthesis">Mechanosynthesis</a></li> <li><a href="/wiki/One-pot_synthesis" title="One-pot synthesis">One-pot synthesis</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Peptide_synthesis" title="Peptide synthesis">Peptide synthesis</a></li> <li><a href="/wiki/Radiosynthesis" title="Radiosynthesis">Radiosynthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthesis</a></li> <li><a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Solid-phase_synthesis" title="Solid-phase synthesis">Solid-phase synthesis</a></li> <li><a href="/wiki/Solvothermal_synthesis" title="Solvothermal synthesis">Solvothermal synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a></li> <li><a href="/wiki/Volume_combustion_synthesis" title="Volume combustion synthesis">Volume combustion synthesis</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, 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href="/wiki/File:Symbol_portal_class.svg" class="mw-file-description" title="Portal"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/16px-Symbol_portal_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/23px-Symbol_portal_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/31px-Symbol_portal_class.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span><b><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Portal</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Concepts_in_enantioselective_synthesis" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Asymmetric_synthesis" title="Template:Asymmetric synthesis"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Asymmetric_synthesis" title="Template talk:Asymmetric synthesis"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Asymmetric_synthesis" title="Special:EditPage/Template:Asymmetric synthesis"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Concepts_in_enantioselective_synthesis" style="font-size:114%;margin:0 4em">Concepts in <a class="mw-selflink selflink">enantioselective synthesis</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chirality types</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">Chirality</a></li> <li><a href="/wiki/Stereocenter" title="Stereocenter">Stereocenter</a></li> <li><a href="/wiki/Planar_chirality" title="Planar chirality">Planar chirality</a></li> <li><a href="/wiki/C2-Symmetric_ligands" title="C2-Symmetric ligands"><i>C</i><sub>2</sub>-symmetric ligands</a></li> <li><a href="/wiki/Axial_chirality" title="Axial chirality">Axial chirality</a></li> <li><a href="/wiki/Supramolecular_chirality" title="Supramolecular chirality">Supramolecular chirality</a></li> <li><a href="/wiki/Inherent_chirality" title="Inherent chirality">Inherent chirality</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chiral molecules</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereoisomerism" title="Stereoisomerism">Stereoisomer</a></li> <li><a href="/wiki/Enantiomer" title="Enantiomer">Enantiomer</a></li> <li><a href="/wiki/Diastereomer" title="Diastereomer">Diastereomer</a></li> <li><a href="/wiki/Meso_compound" title="Meso compound">Meso compound</a></li> <li><a href="/wiki/Racemic_mixture" title="Racemic mixture">Racemic mixture</a></li> <li><a href="/wiki/Enantiomeric_excess" title="Enantiomeric excess">Enantiomeric excess</a> (ee)</li> <li><a href="/wiki/Diastereomeric_excess" class="mw-redirect" title="Diastereomeric excess">Diastereomeric excess</a> (de)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Analysis</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Optical_rotation" title="Optical rotation">Optical rotation</a></li> <li><a href="/wiki/Chiral_derivatizing_agent" title="Chiral derivatizing agent">Chiral derivatizing agents</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy_of_stereoisomers" title="Nuclear magnetic resonance spectroscopy of stereoisomers">NMR spectroscopy of stereoisomers</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy_of_stereoisomers" title="Ultraviolet–visible spectroscopy of stereoisomers">Ultraviolet–visible spectroscopy of stereoisomers</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chiral_resolution" title="Chiral resolution">Chiral resolution</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">Recrystallization</a></li> <li><a href="/wiki/Kinetic_resolution" title="Kinetic resolution">Kinetic resolution</a></li> <li><a href="/wiki/Chiral_column_chromatography" title="Chiral column chromatography">Chiral column chromatography</a></li> <li><a href="/wiki/Diastereomeric_recrystallization" title="Diastereomeric recrystallization">Diastereomeric recrystallization</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asymmetric_induction" title="Asymmetric induction">Asymmetric induction</a></li> <li><a href="/wiki/Chiral_pool_synthesis" class="mw-redirect" title="Chiral pool synthesis">Chiral pool synthesis</a></li> <li><a href="/wiki/Chiral_auxiliary" title="Chiral auxiliary">Chiral auxiliaries</a></li> <li><a href="/wiki/Asymmetric_catalysis" class="mw-redirect" title="Asymmetric catalysis">Asymmetric catalysis</a></li> <li><a href="/wiki/Organocatalysis" title="Organocatalysis">Organocatalysis</a></li> <li><a href="/wiki/Biocatalysis" title="Biocatalysis">Biocatalysis</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Branches_of_chemistry" title="Template:Branches of chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Branches_of_chemistry" title="Template talk:Branches of chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Branches_of_chemistry" title="Special:EditPage/Template:Branches of chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Branches_of_chemistry" style="font-size:114%;margin:0 4em">Branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Glossary_of_chemical_formulae" title="Glossary of chemical formulae">Glossary of chemical formulae</a></li> <li><a href="/wiki/List_of_biomolecules" title="List of biomolecules">List of biomolecules</a></li> <li><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">List of inorganic compounds</a></li> <li><a href="/wiki/Periodic_table" title="Periodic table">Periodic table</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a 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title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a class="mw-selflink selflink">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem 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science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span 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