Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three‐Membered Carbocycles

Zhang Zhi‐Qi; Zheng Meng‐Meng; Xue Xiao‐Song; Marek Ilan; Zhang Fa‐Guang; Ma Jun‐An

摘要

Abstract > Herein we described an efficient Rh II ‐catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO <sub>2</sub> CF <sub>2</sub> CHN <sub>2</sub> , Ps‐DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99?% yield, 97?% ee ). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross‐couplings, hydrogenation, Diels–Alder reaction, and Pauson–Khand reaction. </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> > 在此，我们描述了一种有效的RH ii </ sup> - 用掩蔽的二氟二乙醚试剂（PHSO <sub> 2 </ sub> CF. <sub> 2 </ sub> CHN. <sub> 2 </ sub> ps-dfa）。这种不对称转化提供了高效地获得了广泛的enalioIroched二氟甲基化环烯醇（40个实施例，高达99Ω％的产率，97Ω％ ee </ i> ）。通过随后的立体掺杂方法证明了所得应变碳键碳的合成实用性，包括交叉偶联，氢化，导酰胺反应和Pauson-k手反应。 </ 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>2019年第50期</span><b style="margin: 0 2px;">|</b><span>共6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=Zhang Zhi‐Qi&option=202" target="_blank" rel="nofollow">Zhang Zhi‐Qi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zheng Meng‐Meng&option=202" target="_blank" rel="nofollow">Zheng Meng‐Meng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xue Xiao‐Song&option=202" target="_blank" rel="nofollow">Xue Xiao‐Song;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Marek Ilan&option=202" target="_blank" rel="nofollow">Marek Ilan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Fa‐Guang&option=202" target="_blank" rel="nofollow">Zhang Fa‐Guang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ma Jun‐An&option=202" target="_blank" rel="nofollow">Ma Jun‐An;</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 ChemistryTianjin UniversityTianjin 300072 P. R. China;</p> <p>State Key Laboratory of Elemento-organic ChemistryNankai UniversityTianjin 300071 P. R. China;</p> <p>State Key Laboratory of Elemento-organic ChemistryNankai UniversityTianjin 300071 P. R. China;</p> <p>Schulich Faculty of ChemistryTechnion-Israel Institute of TechnologyHaifa 3200009 Israel;</p> <p>Department of ChemistryTianjin UniversityTianjin 300072 P. R. China;</p> <p>Department of ChemistryTianjin UniversityTianjin 300072 P. R. 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=cyclopropenation&option=203" rel="nofollow">cyclopropenation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=diazo compounds&option=203" rel="nofollow">diazo compounds;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=homogeneous catalysis&option=203" rel="nofollow">homogeneous catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=internal alkynes&option=203" rel="nofollow">internal alkynes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=metal carbenes&option=203" rel="nofollow">metal carbenes;</a> </p> <div class="translation"> 机译：环丙烯;重氮化合物;均匀催化;内部alkynes;金属碳酸盐; </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/0704028165467.html">Back Cover: Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three‐Membered Carbocycles (Angew. 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