Catalytic Enantioselective Benzilic Ester Rearrangement

Wu Hua; Wang Qian; Zhu Jieping

摘要

Abstract > We report the first examples of catalytic enantioselective benzilic ester rearrangement reaction. In the presence of a catalytic amount of Cu(OTf) <sub>2</sub> and a chiral box ligand under mild conditions, reaction of 2,3‐diketoesters with alcohols afforded structurally diverse α‐aryl(alkyl) substituted‐α‐hydroxy malonates (tartronic esters) in good to excellent yields with high enantioselectivities. Preliminary mechanistic studies indicated that hemiketalization, rather than the dynamic kinetic resolution of hemiketal, was the enantiodetermining step under our reaction conditions. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 我们报道了催化对苯硅酸酯重排反应的第一个实例。在存在催化量的Cu（OTF） <sub> 2 </ sub> 在温和条件下的手性盒配体，2,3-一代酯与醇的反应，其具有结构不同α-芳基（烷基）取代 - α-羟基丙二酸酯（Tartronic酯），其优异的产量为高对映射性。初步机械研究表明，半幂化，而不是动态的动态动态分辨率，是在我们的反应条件下的炔酰胺化步骤。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第18期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Hua&option=202" target="_blank" rel="nofollow">Wu Hua;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Qian&option=202" target="_blank" rel="nofollow">Wang Qian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhu Jieping&option=202" target="_blank" rel="nofollow">Zhu Jieping;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Laboratory of Synthesis and Natural ProductsEcole Polytechnique Fédérale de Lausanne1015 Lausanne Switzerland;</p> <p>Laboratory of Synthesis and Natural ProductsEcole Polytechnique Fédérale de Lausanne1015 Lausanne Switzerland;</p> <p>Laboratory of Synthesis and Natural ProductsEcole Polytechnique Fédérale de Lausanne1015 Lausanne Switzerland;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=2&option=203" rel="nofollow">2;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=3-diketoester&option=203" rel="nofollow">3-diketoester;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=asymmetric synthesis&option=203" rel="nofollow">asymmetric synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=benzilic ester rearrangement&option=203" rel="nofollow">benzilic ester rearrangement;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chiral copper catalyst&option=203" rel="nofollow">chiral copper catalyst;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=tartronic esters&option=203" rel="nofollow">tartronic esters;</a> </p> <div class="translation"> 机译：2;3-二酮酯;不对称合成;苯硅酸酯重排;手性铜催化剂;TALTRONIC酯; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 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2013</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061201069849.html">从外消旋4-(1-氨基乙基)苯甲酸甲酯通过脂酶催化的对映选择性酰化反应并随后用硫酸沉淀以制备(R)-和(S)-4-(1-铵乙基)苯甲酸甲酯硫酸盐的方法</a> <b>[P]</b> . <span> 中国专利： CN101321875B </span> <span> . 2012.12.12</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120105524673.html">从外消旋4－(1－氨基乙基)苯甲酸甲酯通过脂酶催化的对映选择性酰化反应并随后用硫酸沉淀以制备(R)－和(S)－4－(1－铵乙基)苯甲酸甲酯硫酸盐的方法</a> <b>[P]</b> . <span> 中国专利： CN101321875A </span> <span> . 2008-12-10</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130483786273.html">Analgesic and spasmolytic benzilic acid derivs prepn - from alpha-(4-hydroxybutoxy)-benzilic acid ester and thionyl chloride</a> <b>[P]</b> . <span> 外国专利：  DE2447807A1 </span> <span> . 1975-04-10</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: 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