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mw-first-heading"><span class="mw-page-title-main">Jacobsen epoxidation</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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.ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Jacobsen epoxidation </th></tr> <tr> <td>Named after </td> <td><a href="/wiki/Eric_N._Jacobsen" class="mw-redirect" title="Eric N. Jacobsen">Eric N. Jacobsen</a> </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td>Organic Chemistry Portal </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/jacobsen-katsuki-epoxidation.shtm">jacobsen-katsuki-epoxidation</a></span> </td></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000686">RXNO:0000686</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Jacobsen%27s_catalysts.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Jacobsen%27s_catalysts.svg/220px-Jacobsen%27s_catalysts.svg.png" decoding="async" width="220" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Jacobsen%27s_catalysts.svg/330px-Jacobsen%27s_catalysts.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Jacobsen%27s_catalysts.svg/440px-Jacobsen%27s_catalysts.svg.png 2x" data-file-width="765" data-file-height="475" /></a><figcaption> <a href="/wiki/Jacobsen%27s_catalyst" title="Jacobsen's catalyst">Jacobsen's catalysts</a><br /> R = Alkyl, <i>O</i>-alkyl, <i>O</i>-trialkyl<br /> Best Jacobsen catalyst: R = <sup>t</sup>Bu</figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Katsukis_catalysts.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Katsukis_catalysts.png/220px-Katsukis_catalysts.png" decoding="async" width="220" height="167" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Katsukis_catalysts.png/330px-Katsukis_catalysts.png 1.5x, //upload.wikimedia.org/wikipedia/commons/e/e7/Katsukis_catalysts.png 2x" data-file-width="343" data-file-height="260" /></a><figcaption> Katsuki's catalysts<br /> R<sup>1</sup> = Aryl, substituted aryl<br /> R<sup>2</sup> = Aryl, Alkyl</figcaption></figure> <p>The <b>Jacobsen <a href="/wiki/Epoxidation" class="mw-redirect" title="Epoxidation">epoxidation</a></b>, sometimes also referred to as <b>Jacobsen-Katsuki epoxidation</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> which allows <a href="/wiki/Enantioselective" class="mw-redirect" title="Enantioselective">enantioselective</a> epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes.<sup id="cite_ref-zhang1990_1-0" class="reference"><a href="#cite_note-zhang1990-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-jacobsen1991_2-0" class="reference"><a href="#cite_note-jacobsen1991-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-katsuki1991_3-0" class="reference"><a href="#cite_note-katsuki1991-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is complementary to the <a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a> (used to form <a href="/wiki/Epoxides" class="mw-redirect" title="Epoxides">epoxides</a> from the double bond in <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>). The Jacobsen epoxidation gains its <a href="/wiki/Stereoselective" class="mw-redirect" title="Stereoselective">stereoselectivity</a> from a <a href="/wiki/Molecular_symmetry#Point_Group" title="Molecular symmetry"><i>C<sub>2</sub></i></a> <a href="/wiki/Molecular_symmetry" title="Molecular symmetry">symmetric</a> <a href="/wiki/Manganese" title="Manganese">manganese(III)</a> <a href="/wiki/Salen_ligand" title="Salen ligand">salen-like ligand</a>, which is used in <a href="/wiki/Catalysis" title="Catalysis">catalytic</a> amounts. The manganese atom transfers an oxygen atom from <a href="/wiki/Chlorine_bleach" class="mw-redirect" title="Chlorine bleach">chlorine bleach</a> or similar oxidant. The reaction takes its name from its inventor, <a href="/wiki/Eric_Jacobsen_(chemist)" title="Eric Jacobsen (chemist)">Eric Jacobsen</a>, with <a href="/wiki/Tsutomu_Katsuki" title="Tsutomu Katsuki">Tsutomu Katsuki</a> sometimes being included. Chiral-directing catalysts are useful to organic chemists trying to control the stereochemistry of biologically active compounds and develop <a href="/wiki/Enantiopure_drug" title="Enantiopure drug">enantiopure drugs</a>. </p><p>Several improved procedures have been developed.<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><sup id="cite_ref-5" class="reference"><a href="#cite_note-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> </p><p>A general reaction scheme follows:<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> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:General_Jacobsen_reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/General_Jacobsen_reaction.png/450px-General_Jacobsen_reaction.png" decoding="async" width="450" height="203" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/General_Jacobsen_reaction.png/675px-General_Jacobsen_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/General_Jacobsen_reaction.png/900px-General_Jacobsen_reaction.png 2x" data-file-width="2352" data-file-height="1061" /></a></span></dd></dl> <meta property="mw:PageProp/toc" /> <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=Jacobsen_epoxidation&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the early 1990s, Jacobsen and Katsuki independently released their initial findings about their catalysts for the enantioselective epoxidation of isolated alkenes.<sup id="cite_ref-zhang1990_1-1" class="reference"><a href="#cite_note-zhang1990-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-katsuki1991_3-1" class="reference"><a href="#cite_note-katsuki1991-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In 1991, Jacobsen published work where he attempted to perfect the catalyst. He was able to obtain ee values above 90% for a variety of ligands. Also, the amount of catalyst used was no more than 15% of the amount of alkene used in the reaction.<sup id="cite_ref-jacobsen1991_2-1" class="reference"><a href="#cite_note-jacobsen1991-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="General_features">General features</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsen_epoxidation&action=edit&section=2" title="Edit section: General features"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The degree of enantioselectivity depends on numerous factors, namely the structure of the alkene, the nature of the axial donor ligand on the active <a href="/wiki/Transition_metal_oxo_complex" title="Transition metal oxo complex">oxomanganese</a> species and the reaction temperature. Cyclic and acyclic <i>cis</i>-1,2-disubstituted alkenes are epoxidized with almost 100% enantioselectivity whereas <i>trans</i>-1,2-disubstituted alkenes are poor substrates for Jacobsen's catalysts but yet give higher enantioselectivities when Katsuki's catalysts are used. Furthermore, the enantioselective epoxidation of conjugated dienes is much higher than that of the nonconjugated dienes.<sup id="cite_ref-Linker1997_8-0" class="reference"><a href="#cite_note-Linker1997-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The enantioselectivity is explained by either a "top-on" approach (Jacobsen) or by a "side-on" approach (Katsuki) of the alkene. </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsen_epoxidation&action=edit&section=3" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mechanism of the Jacobsen–Katsuki epoxidation is not fully understood, but most likely a manganese(V)-species (similar to the <a href="/wiki/High-valent_iron" title="High-valent iron">ferryl</a> intermediate of <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">Cytochrome P450</a>) is the reactive intermediate which is formed upon the oxidation of the Mn(III)-<a href="/wiki/Salen_complex" class="mw-redirect" title="Salen complex">salen complex</a>. There are three major pathways. The concerted pathway, the metalla oxetane pathway and the radical pathway. The most accepted mechanism is the concerted pathway mechanism. After the formation of the Mn(V) complex, the catalyst is activated and therefore can form epoxides with alkenes. The alkene comes in from the "top-on" approach (above the plane of the catalyst) and the oxygen atom now is bonded to the two carbon atoms (previously C=C bond) and is still bonded to the manganese metal. Then, the Mn–O bond breaks and the epoxide is formed. The Mn(III)-salen complex is regenerated, which can then be oxidized again to form the Mn(V) complex.<sup id="cite_ref-jacobsen1991_2-2" class="reference"><a href="#cite_note-jacobsen1991-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-katsuki1991_3-2" class="reference"><a href="#cite_note-katsuki1991-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png" class="mw-file-description" title="Mechanism of the Jacobsen catalytic enantioselective epoxidation"><img alt="Mechanism of the Jacobsen catalytic enantioselective epoxidation" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png/250px-Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png" decoding="async" width="250" height="305" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png/375px-Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png/500px-Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png 2x" data-file-width="2477" data-file-height="3017" /></a><figcaption>Mechanism of the Jacobsen catalytic enantioselective epoxidation</figcaption></figure></dd></dl> <p>The radical intermediate accounts for the formation of mixed epoxides when conjugated dienes are used as substrates.<sup id="cite_ref-Linker1997_8-1" class="reference"><a href="#cite_note-Linker1997-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png" class="mw-file-description" title="Mechanisms of the free-radical and metallo-oxetane pathways of the Jacobsen-Katsuki reaction"><img alt="Mechanisms of the free-radical and metallo-oxetane pathways of the Jacobsen-Katsuki reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png/600px-Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png" decoding="async" width="600" height="233" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png/900px-Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png/1200px-Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png 2x" data-file-width="6233" data-file-height="2419" /></a><figcaption>Mechanisms of the free-radical and metallo-oxetane pathways of the Jacobsen-Katsuki reaction</figcaption></figure></dd></dl> <p>Dimethyldioxirane]] can be used as a source of O atomes.DMD of a chiral metal catalyst followed by epoxidation, or (2) epoxidation by chiral dioxiranes, which are generated <i>in situ</i> from a catalytic amount of ketone and a stoichiometric amount of a terminal oxidant).<sup id="cite_ref-Shi_9-0" class="reference"><a href="#cite_note-Shi-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Mn-<a href="/wiki/Salen_complexes" class="mw-redirect" title="Salen complexes">salen complexes</a> have been used with success to accomplish the first strategy.<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> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:DOEpoxStereo2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/2/26/DOEpoxStereo2.png" decoding="async" width="507" height="268" class="mw-file-element" data-file-width="507" data-file-height="268" /></a></span></dd></dl> <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=Jacobsen_epoxidation&action=edit&section=4" 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"><ol class="references"> <li id="cite_note-zhang1990-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-zhang1990_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-zhang1990_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFZhangLoebachWilsonJacobsen1990" class="citation journal cs1">Zhang, W.; Loebach, J. L.; Wilson, S. R.; <a href="/wiki/Eric_Jacobsen_(chemist)" title="Eric Jacobsen (chemist)">Jacobsen, E. N.</a> (March 1990). 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"Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane". <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. <b>113</b> (18): 7063. <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%2Fja00018a068">10.1021/ja00018a068</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+American+Chemical+Society&rft.atitle=Highly+enantioselective+epoxidation+catalysts+derived+from+1%2C2-diaminocyclohexane&rft.volume=113&rft.issue=18&rft.pages=7063&rft.date=1991&rft_id=info%3Adoi%2F10.1021%2Fja00018a068&rft.aulast=Jacobsen&rft.aufirst=Eric+N.&rft.au=Zhang%2C+Wei&rft.au=Muci%2C+Alexander+R.&rft.au=Ecker%2C+James+R.&rft.au=Deng%2C+Li&rfr_id=info%3Asid%2Fen.wikipedia.org%3AJacobsen+epoxidation" class="Z3988"></span></span> </li> <li id="cite_note-katsuki1991-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-katsuki1991_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-katsuki1991_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-katsuki1991_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIrie,_R.Noda,_K.Ito,_Y.Matsumoto,_N.1991" class="citation journal cs1">Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. (1991). "Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes". <i><a href="/w/index.php?title=Tetrahedron:_Asymmetry&action=edit&redlink=1" class="new" title="Tetrahedron: Asymmetry (page does not exist)">Tetrahedron: Asymmetry</a></i>. <b>2</b> (7): <span class="nowrap">481–</span>494. <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%2FS0957-4166%2800%2986102-9">10.1016/S0957-4166(00)86102-9</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron%3A+Asymmetry&rft.atitle=Catalytic+asymmetric+epoxidation+of+unfunctionalized+olefins+using+chiral+%28salen%29manganese%28III%29+complexes&rft.volume=2&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E481-%3C%2Fspan%3E494&rft.date=1991&rft_id=info%3Adoi%2F10.1016%2FS0957-4166%2800%2986102-9&rft.au=Irie%2C+R.&rft.au=Noda%2C+K.&rft.au=Ito%2C+Y.&rft.au=Matsumoto%2C+N.&rft.au=Katsuki%2C+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AJacobsen+epoxidation" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFE._N._JacobsenDengFurukawaMartínez1994" class="citation journal cs1"><a href="/wiki/Eric_Jacobsen_(chemist)" title="Eric Jacobsen (chemist)">E. 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"Enantioselective Catalytic Epoxidation of Cinnamate Esters". <i><a href="/wiki/Tetrahedron_(journal)" title="Tetrahedron (journal)">Tetrahedron</a></i>. <b>50</b> (15): <span class="nowrap">4323–</span>4334. <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%2FS0040-4020%2801%2989369-8">10.1016/S0040-4020(01)89369-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Enantioselective+Catalytic+Epoxidation+of+Cinnamate+Esters&rft.volume=50&rft.issue=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4323-%3C%2Fspan%3E4334&rft.date=1994&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2801%2989369-8&rft.au=E.+N.+Jacobsen&rft.au=Deng%2C+L.&rft.au=Furukawa%2C+Y.&rft.au=Mart%C3%ADnez%2C+L.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AJacobsen+epoxidation" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChang,_S.Galvin,_J._M.E._N._Jacobsen1994" class="citation journal cs1">Chang, S.; Galvin, J. M.; <a href="/wiki/Eric_Jacobsen_(chemist)" title="Eric Jacobsen (chemist)">E. N. Jacobsen</a> (1994). "Effect of Chiral Quaternary Ammonium Salts on (salen)Mn-Catalyzed Epoxidation of <i>Cis</i>-Olefins. A Highly Enantioselective, Catalytic Route to <i>Trans</i>-Epoxides". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. 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Engl.</a></i> <b>36</b> (19): <span class="nowrap">2060–</span>2062. <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%2Fanie.199720601">10.1002/anie.199720601</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&rft.atitle=Jacobsen-Katsuki+epoxidation+and+its+controversial+mechanism&rft.volume=36&rft.issue=19&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2060-%3C%2Fspan%3E2062&rft.date=1997&rft_id=info%3Adoi%2F10.1002%2Fanie.199720601&rft.au=Linker%2C+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AJacobsen+epoxidation" class="Z3988"></span></span> </li> <li id="cite_note-Shi-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-Shi_9-0">^</a></b></span> <span class="reference-text">Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. <i>J. Am. Chem. 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T.; Gessner, R.; Patonay, T.; Simon, A.; Tóth, G. <i>Tetrahedron</i> <b>1998</b>, <i>54</i>, 13105.</span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Jacobsen_epoxidation&oldid=1202054144">https://en.wikipedia.org/w/index.php?title=Jacobsen_epoxidation&oldid=1202054144</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Ring_forming_reactions" title="Category:Ring forming reactions">Ring forming reactions</a></li><li><a href="/wiki/Category:Epoxidation_reactions" title="Category:Epoxidation reactions">Epoxidation reactions</a></li><li><a href="/wiki/Category:Organic_oxidation_reactions" title="Category:Organic oxidation reactions">Organic oxidation reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 1 February 2024, at 23:18<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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