Synthesis of Axially Chiral Styrenes through Pd‐Catalyzed Asymmetric C?H Olefination Enabled by an Amino Amide Transient Directing Group

Song Hong; Li Ya; Yao Qi‐Jun; Jin Liang; Liu Lei; Liu Yan‐Hua; Shi Bing‐Feng

摘要

Abstract > The atroposelective synthesis of axially chiral styrenes remains a formidable challenge due to their relatively lower rotational barriers compared to the biaryl atropoisomers. Herein, we describe the construction of axially chiral styrenes through Pd II ‐catalyzed atroposelective C?H olefination, using a bulky amino amide as a transient chiral auxiliary. Various axially chiral styrenes were produced with good yields and high enantioselectivity (up to 95?% yield and 99?% ee ). Carboxylic acid derivatives of the resulting axially chiral styrenes showed superior enantiocontrol over the biaryl counterparts in Co III ‐catalyzed enantioselective C(sp 3 )?H amidation of thioamide. Mechanistic studies suggest that C?H cleavage is the enantioselectivity‐determining step. </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> > 轴向手性苯乙烯的阿巴泊素选择性合成仍然是与与前丙酮异构体相比相对较低的旋转屏障引起的突起攻击。在此，我们通过PD描述轴向手性苯乙烯的构造 ii </ sup> - 使用庞大的氨基酰胺作为瞬时手性助剂，催化AtropoSelective C'H烯烃。生产各种轴向手性苯乙烯，产率良好，高映射率高（高达95〜％收率，99？％ ee </ i> ）。所得轴向手性苯乙烯的羧酸衍生物在CO中的前列子组上显示出优异的肾上腺酮 iii </ sup> -Catalyzed对映选择性C（SP 3 </ sup> ）？H胺酰胺化。机械研究表明C？H切割是对映的决定步骤。 </ 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16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=Song Hong&option=202" target="_blank" rel="nofollow">Song Hong;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Ya&option=202" target="_blank" rel="nofollow">Li Ya;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yao Qi‐Jun&option=202" target="_blank" rel="nofollow">Yao Qi‐Jun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jin Liang&option=202" target="_blank" rel="nofollow">Jin Liang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Lei&option=202" target="_blank" rel="nofollow">Liu Lei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Yan‐Hua&option=202" target="_blank" rel="nofollow">Liu Yan‐Hua;</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> <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=axially chiral styrenes&option=203" rel="nofollow">axially chiral styrenes;</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=palladium&option=203" rel="nofollow">palladium;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=transient directing groups&option=203" rel="nofollow">transient directing groups;</a> </p> <div class="translation"> 机译：AtropoSelectivity;轴向手性苯乙烯;C？H烯烯;钯;瞬态指导组; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704028161275.html">Synthesis of Axially Chiral Styrenes through Pd‐Catalyzed Asymmetric C?H Olefination Enabled by an Amino Amide Transient Directing Group</a> <b>[J]</b> . <span> 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