Synthesis of Axially Chiral Biaryl‐2‐amines by PdII‐Catalyzed Free‐Amine‐Directed Atroposelective C?H Olefination

Zhan Bei‐Bei; Wang Lei; Luo Jun; Lin Xu‐Feng; Shi Bing‐Feng

摘要

Abstract > A simple and ubiquitously present group, free amine, is used as a directing group to synthesize axially chiral biaryl compounds by Pd II ‐catalyzed atroposelective C?H olefination. A broad range of axially chiral biaryl‐2‐amines can be obtained in good yields with high enantioselectivities (up to 97?% ee ). Chiral spiro phosphoric acid (SPA) proved to be an efficient ligand and the loading could be reduced to 1?mol?% without erosion of enantiocontrol in gram‐scale synthesis. The resulting axially chiral biaryl‐2‐amines also provide a platform for the synthesis of a set of chiral ligands. </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> > 本发明的单纯性和普遍存在的基团，游离胺用作引导基团，通过PD合成轴向手性的芳基化合物 ii </ sup> - 催化的AtroposElective C？H烯烃。宽范围的轴向手性辅导胺-2-胺可以良好的产量，高对映射性（高达97？％ ee </ i> ）。手性螺磷酸（SPA）被证明是一种有效的配体，并且负载可以将1？摩尔α％降低至1？摩尔·％，而不会在革兰氏型合成中侵蚀肾上腺素。由此产生的轴向手性的Biarall-2-胺还提供了一组手性配体的合成的平台。 </ 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9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=Zhan Bei‐Bei&option=202" target="_blank" rel="nofollow">Zhan Bei‐Bei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Lei&option=202" target="_blank" rel="nofollow">Wang Lei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Luo Jun&option=202" target="_blank" rel="nofollow">Luo Jun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lin Xu‐Feng&option=202" target="_blank" rel="nofollow">Lin Xu‐Feng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Shi Bing‐Feng&option=202" target="_blank" rel="nofollow">Shi Bing‐Feng;</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>Department of ChemistryZhejiang UniversityHangzhou 310027 China;</p> <p>Department of ChemistryZhejiang UniversityHangzhou 310027 China;</p> <p>Department of ChemistryZhejiang UniversityHangzhou 310027 China;</p> <p>Department of ChemistryZhejiang UniversityHangzhou 310027 China;</p> <p>Department of ChemistryZhejiang UniversityHangzhou 310027 China;</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=atroposelectivity&option=203" rel="nofollow">atroposelectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=biaryl-2-amines&option=203" rel="nofollow">biaryl-2-amines;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=C?H olefination&option=203" rel="nofollow">C?H olefination;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chiral spiro phosphoric acids&option=203" rel="nofollow">chiral spiro phosphoric acids;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=palladium&option=203" rel="nofollow">palladium;</a> </p> <div class="translation"> 机译：AtropoSelectivity;芳丙烯酸二胺;C？H烯胺;手性螺磷酸;钯; 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href="/patent-detail/06120100637969.html">一种钯催化不对称C-H键胺羰基化合成手性异喹啉的方法</a> <b>[P]</b> . <span> 中国专利： CN109810057A </span> <span> . 2019-05-28</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120120569.html">异丙胺合成二异丙胺、三异丙胺的催化剂及工艺</a> <b>[P]</b> . <span> 中国专利： CN1127373C </span> <span> . 2003.11.12</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130449702245.html">Enzymatic synthesis of chiral amines using -2-amino propane as amine donor</a> <b>[P]</b> . <span> 外国专利：  US6133018A </span> <span> . 2000-10-17</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：以-2-氨基丙烷为胺供体的酶法合成手性胺 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130433835974.html">METHOD FOR DESIGNING ENZYME FOR CATALYZING DIRECT CONDENSATION REACTION OF FREE CARBOXYLIC ACID 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