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<div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Externí odkazy</span> </div> </a> <ul id="toc-Externí_odkazy-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Obsah" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Obsah" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Přepnout obsah" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Přepnout obsah</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Jacobsenova epoxidace</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="Přejděte k článku v jiném jazyce. Je dostupný v 8 jazycích" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-8" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">8 jazyků</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Jacobsen-Epoxidierung" title="Jacobsen-Epoxidierung – němčina" lang="de" hreflang="de" data-title="Jacobsen-Epoxidierung" data-language-autonym="Deutsch" data-language-local-name="němčina" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Jacobsen_epoxidation" title="Jacobsen epoxidation – angličtina" lang="en" hreflang="en" data-title="Jacobsen epoxidation" data-language-autonym="English" data-language-local-name="angličtina" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%BE%D9%88%DA%A9%D8%B3%DB%8C%D8%AF%D8%A7%D8%B3%DB%8C%D9%88%D9%86_%D8%AC%DB%8C%DA%A9%D9%88%D8%A8%D8%B3%D9%86" title="اپوکسیداسیون جیکوبسن – perština" lang="fa" hreflang="fa" data-title="اپوکسیداسیون جیکوبسن" data-language-autonym="فارسی" data-language-local-name="perština" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Jacobsen-epoksidointi" title="Jacobsen-epoksidointi – finština" lang="fi" hreflang="fi" data-title="Jacobsen-epoksidointi" data-language-autonym="Suomi" data-language-local-name="finština" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89poxydation_de_Jacobsen" title="Époxydation de Jacobsen – francouzština" lang="fr" hreflang="fr" data-title="Époxydation de Jacobsen" data-language-autonym="Français" data-language-local-name="francouzština" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Epossidazione_di_Jacobsen" title="Epossidazione di Jacobsen – italština" lang="it" hreflang="it" data-title="Epossidazione di Jacobsen" data-language-autonym="Italiano" data-language-local-name="italština" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B8%E3%82%A7%E3%82%A4%E3%82%B3%E3%83%96%E3%82%BB%E3%83%B3%E3%83%BB%E9%A6%99%E6%9C%88%E3%82%A8%E3%83%9D%E3%82%AD%E3%82%B7%E5%8C%96" title="ジェイコブセン・香月エポキシ化 – japonština" lang="ja" hreflang="ja" data-title="ジェイコブセン・香月エポキシ化" data-language-autonym="日本語" data-language-local-name="japonština" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%9B%85%E5%90%84%E5%B8%83%E6%A3%AE%E7%8E%AF%E6%B0%A7%E5%8C%96%E5%8F%8D%E5%BA%94" title="雅各布森环氧化反应 – čínština" lang="zh" hreflang="zh" data-title="雅各布森环氧化反应" data-language-autonym="中文" data-language-local-name="čínština" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q904749#sitelinks-wikipedia" title="Editovat mezijazykové odkazy" class="wbc-editpage">Upravit odkazy</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Jmenné prostory"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Jacobsenova_epoxidace" title="Zobrazit obsahovou stránku [c]" accesskey="c"><span>Článek</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Diskuse:Jacobsenova_epoxidace" rel="discussion" title="Diskuse ke stránce [t]" accesskey="t"><span>Diskuse</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" 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vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Nástroje</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">přesunout do postranního panelu</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">skrýt</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="Další možnosti" > <div class="vector-menu-heading"> Akce </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected 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href="/wiki/Speci%C3%A1ln%C3%AD:Co_odkazuje_na/Jacobsenova_epoxidace" title="Seznam všech wikistránek, které sem odkazují [j]" accesskey="j"><span>Odkazuje sem</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Speci%C3%A1ln%C3%AD:Souvisej%C3%ADc%C3%AD_zm%C4%9Bny/Jacobsenova_epoxidace" rel="nofollow" title="Nedávné změny stránek, na které je odkazováno [k]" accesskey="k"><span>Související změny</span></a></li><li id="t-upload" class="mw-list-item"><a href="//commons.wikimedia.org/wiki/Special:UploadWizard?uselang=cs" title="Nahrát obrázky či jiná multimédia [u]" accesskey="u"><span>Načíst soubor</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Jacobsenova_epoxidace&oldid=20330932" title="Trvalý odkaz na současnou verzi této stránky"><span>Trvalý odkaz</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Jacobsenova_epoxidace&action=info" title="Více informací o této stránce"><span>Informace o 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Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q904749" title="Odkaz na propojenou položku datového úložiště [g]" accesskey="g"><span>Položka Wikidat</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Nástroje ke stránce"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Vzhled"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Vzhled</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">přesunout do postranního panelu</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">skrýt</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">Z Wikipedie, otevřené encyklopedie</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="cs" dir="ltr"><p><b>Jacobsenova epoxidace</b> (také nazývaná <b>Jacobsenova-Katsukiho epoxidace</b>) je organická reakce, která umožňuje <a href="/wiki/Asymetrick%C3%A1_synt%C3%A9za" title="Asymetrická syntéza">enantioselektivní</a> <a href="/wiki/Epoxidace" class="mw-redirect" title="Epoxidace">epoxidaci</a> <a href="/wiki/Alkeny" title="Alkeny">alkenů</a> substituovaných <a href="/wiki/Alkyl" title="Alkyl">alkylovými</a> a <a href="/wiki/Aryl" title="Aryl">arylovými</a> skupinami.<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> Jde o doplňkovou reakci k <a href="/wiki/Sharplessova_epoxidace" title="Sharplessova epoxidace">Sharplessově epoxidaci</a> (při které se epoxidy připravují pomocí dvojné vazby <a href="/wiki/Allyl" title="Allyl">allylových</a> <a href="/wiki/Alkoholy" title="Alkoholy">alkoholů</a>). <a href="/wiki/Stereoselektivita" title="Stereoselektivita">Stereoselektivita</a> Jacobsenovy epoxidace je způsobena <i>C<sub>2</sub></i> symetrií komplexu ligandu <a href="/wiki/Salen" title="Salen">salenového</a> typu s trojmocným <a href="/wiki/Mangan" title="Mangan">manganem</a>, který se používá jako <a href="/wiki/Katalyz%C3%A1tor" title="Katalyzátor">katalyzátor</a> a přenáší kyslíkový atom z <a href="/wiki/Oxida%C4%8Dn%C3%AD_%C4%8Dinidlo" title="Oxidační činidlo">oxidačního činidla</a>. Katalyzátory ovlivňující chiralitu produktů se používají k dosažení stereoselektivity, což má význam v syntéze biologicky aktivních látek a enantiomerně čistých léčiv. </p><p>Reakce je pojmenována po jejím objeviteli, kterým byl <a href="/w/index.php?title=Eric_Jacobsen&action=edit&redlink=1" class="new" title="Eric Jacobsen (stránka neexistuje)">Eric Jacobsen</a> (někdy se též uvádí <a href="/w/index.php?title=Cutomu_Katsuki&action=edit&redlink=1" class="new" title="Cutomu Katsuki (stránka neexistuje)">Cutomu Katsuki</a>). </p><p>Bylo provedeno několik vylepšení této reakce.<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>Schéma obecné Jacobsenovy reakce vypadá takto:<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/Soubor: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="Historie">Historie</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsenova_epoxidace&veaction=edit&section=1" title="Editace sekce: Historie" class="mw-editsection-visualeditor"><span>editovat</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Jacobsenova_epoxidace&action=edit&section=1" title="Editovat zdrojový kód sekce Historie"><span>editovat zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Na začátku 90. let 20. století Eric Jacobsen A Cutomu Katsuki nezávisle na sobě objevili katalyzátory enantioselektivní epoxidace izolovaných alkenů.<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> Roku 1991 publikoval Jacobsen práci, ve které se snažil najít nejvhodnější katalyzátor. Dokázal dosáhnout <a href="/wiki/Enantiomern%C3%AD_p%C5%99ebytek" title="Enantiomerní přebytek">enantiomerního přebytku</a> přes 90 % u mnoha různých ligandů. Potřebné množství katalyzátoru představovalo méně než 15 % množství alkenu.<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="Vlastnosti">Vlastnosti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsenova_epoxidace&veaction=edit&section=2" title="Editace sekce: Vlastnosti" class="mw-editsection-visualeditor"><span>editovat</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Jacobsenova_epoxidace&action=edit&section=2" title="Editovat zdrojový kód sekce Vlastnosti"><span>editovat zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Enantioselektivita Jacobsenovy epoxidace závisí na mnoha vlivech, jako jsou struktura použitého alkenu, vlastnosti donorového ligandu a teplota. Cyklické i acyklické <i>cis</i>-1,2-disubstituované alkeny se epoxidují s téměř 100% enantioselektivitou, zatímco <i>trans</i>-1,2-disubstituované alkeny špatně reagují při použití Jacobsenových katalyzátorů, ovšem za přítomnosti Katsukiových katalyzátorů reagují lépe. U konjugovaných dienů je enantioselektivita epoxidace mnohem lepší než u nekonjugovaných.<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> <div class="mw-heading mw-heading2"><h2 id="Mechanismus">Mechanismus</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsenova_epoxidace&veaction=edit&section=3" title="Editace sekce: Mechanismus" class="mw-editsection-visualeditor"><span>editovat</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Jacobsenova_epoxidace&action=edit&section=3" title="Editovat zdrojový kód sekce Mechanismus"><span>editovat zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Reak%C4%8Dn%C3%AD_mechanismus" title="Reakční mechanismus">Mechanismus</a> Jacobsenovy epoxidace není zcela znám, ovšem předpokládá se, že reaktivním meziproduktem je manganičná sloučenina, která se tvoří oxidací komplexu trojmocného manganu se <a href="/wiki/Salen" title="Salen">salenem</a>. Navrženy byly tři mechanismy, soustředěný, metaloxetanový a radikálový. Nejpravděpodobnější je soustředěný mechanismus. Při něm po vzniku manganičného komplexu dochází k aktivaci katalyzátoru, který tak může z alkenů vytvořit epoxidy. Atom kyslíku se naváže na dva uhlíkové atomy (mezi nimiž byla původně dvojná vazba), přičemž je stále vázán k manganu. Následně zanikne vazba Mn–O a vytvoří se epoxid. Komplex trojmocného manganu se salenem se obnoví a může se znovu oxidovat.<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/Soubor:Mechanism_of_the_Jacobsen_catalytic_enantioselective_epoxidation.png" class="mw-file-description" title="Mechanismus Jacobsenovy katalytické enantioselektivní epoxidace"><img alt="Mechanismus Jacobsenovy katalytické enantioselektivní epoxidace" 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>Mechanismus Jacobsenovy katalytické enantioselektivní epoxidace</figcaption></figure></dd></dl> <p>Při použití konjugovaných dienů jako substrátů se vytváří radikálový meziprodukt, který přispívá k vytváření směsi dvou produktů.<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/Soubor:Mechanisms_of_the_free-radical_and_metallo-oxetane_pathways_of_the_Jacobsen-Katsuki_reaction.png" class="mw-file-description" title="Radikálový a metalo-oxetanový mechanismus Jacobsenovy-Katsukiovy epoxidace"><img alt="Radikálový a metalo-oxetanový mechanismus Jacobsenovy-Katsukiovy epoxidace" 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>Radikálový a metalo-oxetanový mechanismus Jacobsenovy-Katsukiovy epoxidace</figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reference">Reference</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsenova_epoxidace&veaction=edit&section=4" title="Editace sekce: Reference" class="mw-editsection-visualeditor"><span>editovat</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Jacobsenova_epoxidace&action=edit&section=4" title="Editovat zdrojový kód sekce Reference"><span>editovat zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="plainlinks"><i>V tomto článku byl použit <a href="/wiki/Wikipedie:WikiProjekt_P%C5%99eklad/Rady" title="Wikipedie:WikiProjekt Překlad/Rady">překlad</a> textu z článku <a class="external text" href="https://en.wikipedia.org/wiki/Jacobsen_epoxidation?oldid=885989677"><span class="cizojazycne" lang="en" title="angličtina">Jacobsen epoxidation</span></a> na anglické Wikipedii.</i></span> </p> <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 style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-zhang1990_1-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a></span> <span class="reference-text"><cite style="font-style:normal;">W. Zhang; J. L. Loebach; S. R. Wilson; <a href="/w/index.php?title=Eric_Jacobsen&action=edit&redlink=1" class="new" title="Eric Jacobsen (stránka neexistuje)">E. N. Jacobsen</a>. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes. <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>. 1990, s. 2801–2803.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=%5B%5BJournal+of+the+American+Chemical+Society%5D%5D&rft.atitle=Enantioselective+epoxidation+of+unfunctionalized+olefins+catalyzed+by+salen+manganese+complexes&rft.date=1990&rft.pages=2801%E2%80%932803&rft.au=W.+Zhang&rft.au=J.+L.+Loebach&rft.au=S.+R.+Wilson"><span style="display:none"> </span></span></span> </li> <li id="cite_note-jacobsen1991-2"><span class="mw-cite-backlink">↑ <a href="#cite_ref-jacobsen1991_2-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-jacobsen1991_2-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a> <a href="#cite_ref-jacobsen1991_2-2"><sup style="font-style: italic; font-weight: bold; vertical-align: top">c</sup></a></span> <span class="reference-text"><cite style="font-style:normal;">Eric N. Jacobsen; W. Zhang; Alexander R. Muci; James R. Ecker; Li Deng. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane. <i>Journal of the American Chemical Society</i>. 1991, s. 7063.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Highly+enantioselective+epoxidation+catalysts+derived+from+1%2C2-diaminocyclohexane&rft.date=1991&rft.pages=7063&rft.au=Eric+N.+Jacobsen&rft.au=W.+Zhang&rft.au=Alexander+R.+Muci"><span style="display:none"> </span></span></span> </li> <li id="cite_note-katsuki1991-3"><span class="mw-cite-backlink">↑ <a href="#cite_ref-katsuki1991_3-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-katsuki1991_3-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a> <a href="#cite_ref-katsuki1991_3-2"><sup style="font-style: italic; font-weight: bold; vertical-align: top">c</sup></a></span> <span class="reference-text"><cite style="font-style:normal;">R. Irie; K. Noda; Y. Ito; N. Matsumoto; T. Katsuki. Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes. <i>Tetrahedron: Asymmetry</i>. 1991, s. 481–494.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=Tetrahedron%3A+Asymmetry&rft.atitle=Catalytic+asymmetric+epoxidation+of+unfunctionalized+olefins+using+chiral+%28salen%29manganese%28III%29+complexes&rft.date=1991&rft.pages=481%E2%80%93494&rft.au=R.+Irie&rft.au=K.+Noda&rft.au=Y.+Ito"><span style="display:none"> </span></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text"><cite style="font-style:normal;"><a href="/w/index.php?title=Eric_Jacobsen&action=edit&redlink=1" class="new" title="Eric Jacobsen (stránka neexistuje)">E. N. Jacobsen</a>; L. Deng; Y. Furukawa; L. E. Martínez. Enantioselective Catalytic Epoxidation of Cinnamate Esters. <i><a href="/w/index.php?title=Tetrahedron&action=edit&redlink=1" class="new" title="Tetrahedron (stránka neexistuje)">Tetrahedron</a></i>. 1994, s. 4323–4334.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=%5B%5BTetrahedron%5D%5D&rft.atitle=Enantioselective+Catalytic+Epoxidation+of+Cinnamate+Esters&rft.date=1994&rft.pages=4323%E2%80%934334&rft.au=%5B%5BEric+Jacobsen%7CE.+N.+Jacobsen%5D%5D&rft.au=L.+Deng&rft.au=Y.+Furukawa"><span style="display:none"> </span></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><cite style="font-style:normal;">S. Chang; J. M. Galvin; E. N. Jacobsen. 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/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. 1994, s. 6937–6938.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=%5B%5BJournal+of+the+American+Chemical+Society%5D%5D&rft.atitle=Effect+of+Chiral+Quaternary+Ammonium+Salts+on+%28salen%29Mn-Catalyzed+Epoxidation+of+%27%27Cis%27%27-Olefins.+A+Highly+Enantioselective%2C+Catalytic+Route+to+%27%27Trans%27%27-Epoxides&rft.date=1994&rft.pages=6937%E2%80%936938&rft.au=S.+Chang&rft.au=J.+M.+Galvin&rft.au=E.+N.+Jacobsen"><span style="display:none"> </span></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text"><cite style="font-style:normal;">B. D. Brandes; E. N. Jacobsen. Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins. <i><a href="/w/index.php?title=The_Journal_of_Organic_Chemistry&action=edit&redlink=1" class="new" title="The Journal of Organic Chemistry (stránka neexistuje)">The Journal of Organic Chemistry</a></i>. 1994, s. 4378–4380.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=%5B%5BThe+Journal+of+Organic+Chemistry%5D%5D&rft.atitle=Highly+Enantioselective%2C+Catalytic+Epoxidation+of+Trisubstituted+Olefins&rft.date=1994&rft.pages=4378%E2%80%934380&rft.au=B.+D.+Brandes&rft.au=E.+N.+Jacobsen"><span style="display:none"> </span></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text"><cite class="book" style="font-style:normal;"> <i>Jacobsen Epoxidation</i> [online]. Organic Chemistry Portal [cit. 2009-09-22]. <a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/jacobsen-katsuki-epoxidation.shtm">Dostupné online</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/cs.wikipedia.org:templatecitaceelmonografie&rft.btitle=Jacobsen+Epoxidation&rft_id=https%3A%2F%2Fwww.organic-chemistry.org%2Fnamedreactions%2Fjacobsen-katsuki-epoxidation.shtm&rft.pub=Organic+Chemistry+Portal"><span style="display:none"> </span></span></span> </li> <li id="cite_note-Linker1997-8"><span class="mw-cite-backlink">↑ <a href="#cite_ref-Linker1997_8-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-Linker1997_8-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a></span> <span class="reference-text"><cite style="font-style:normal;">T. Linker. Jacobsen-Katsuki epoxidation and its controversial mechanism. <i><a href="/w/index.php?title=Angewandte_Chemie&action=edit&redlink=1" class="new" title="Angewandte Chemie (stránka neexistuje)">Angewandte Chemie International Edition in English</a></i>. 1997, s. 2060–2062.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/cs.wikipedia.org:templatecitaceperiodika&rft.jtitle=%5B%5BAngewandte+Chemie%7CAngewandte+Chemie+International+Edition+in+English%5D%5D&rft.atitle=Jacobsen-Katsuki+epoxidation+and+its+controversial+mechanism&rft.date=1997&rft.pages=2060%E2%80%932062&rft.au=T.+Linker"><span style="display:none"> </span></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Externí_odkazy"><span id="Extern.C3.AD_odkazy"></span>Externí odkazy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Jacobsenova_epoxidace&veaction=edit&section=5" title="Editace sekce: Externí odkazy" class="mw-editsection-visualeditor"><span>editovat</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Jacobsenova_epoxidace&action=edit&section=5" title="Editovat zdrojový kód sekce Externí odkazy"><span>editovat zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="wd"><span class="sisterproject sisterproject-commons"><span class="sisterproject_image"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></span> <span class="sisterproject_text">Obrázky, zvuky či videa k tématu <span class="sisterproject_text_target"><a href="https://commons.wikimedia.org/wiki/Category:Jacobsen_epoxidation" class="extiw" title="c:Category:Jacobsen epoxidation">Jacobsenova epoxidace</a></span> na Wikimedia Commons</span></span></span><i> </i></li></ul> <style data-mw-deduplicate="TemplateStyles:r23078045">.mw-parser-output .navbox2{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox2 .navbox2{margin-top:0}.mw-parser-output .navbox2+.navbox2{margin-top:-1px}.mw-parser-output .navbox2-inner,.mw-parser-output .navbox2-subgroup{width:100%}.mw-parser-output .navbox2-group,.mw-parser-output .navbox2-title,.mw-parser-output .navbox2-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output th.navbox2-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox2,.mw-parser-output .navbox2-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox2-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output tr+tr>.navbox2-abovebelow,.mw-parser-output tr+tr>.navbox2-group,.mw-parser-output tr+tr>.navbox2-image,.mw-parser-output tr+tr>.navbox2-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox2 th,.mw-parser-output .navbox2-title{background-color:#e0e0e0}.mw-parser-output .navbox2-abovebelow,.mw-parser-output th.navbox2-group,.mw-parser-output .navbox2-subgroup .navbox2-title{background-color:#e7e7e7}.mw-parser-output .navbox2-subgroup .navbox2-title{font-size:88%}.mw-parser-output .navbox2-subgroup .navbox2-group,.mw-parser-output .navbox2-subgroup .navbox2-abovebelow{background-color:#f0f0f0}.mw-parser-output .navbox2-even{background-color:#f7f7f7}.mw-parser-output .navbox2-odd{background-color:transparent}.mw-parser-output .navbox2 .hlist td dl,.mw-parser-output .navbox2 .hlist td ol,.mw-parser-output .navbox2 .hlist td ul,.mw-parser-output .navbox2 td.hlist dl,.mw-parser-output .navbox2 td.hlist ol,.mw-parser-output .navbox2 td.hlist ul{padding:0.125em 0}</style> <style data-mw-deduplicate="TemplateStyles:r16915398">.mw-parser-output div/**/#portallinks a{font-weight:bold}</style><div id="portallinks" class="catlinks"><a href="/wiki/Port%C3%A1l:Obsah" title="Portál:Obsah">Portály</a>: <a href="/wiki/Port%C3%A1l:Chemie" title="Portál:Chemie">Chemie</a> </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; 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