Highly Enantioselective Construction of Strained Spiro[2,3]hexanes through a Michael Addition/Ring Expansion/Cyclization Cascade

Zhao Chuan‐Gang; Feng Zhi‐Tao; Xu Guo‐Qiang; Gao Ang; Chen Jing‐Wei; Wang Zhu‐Yin; Xu Peng‐Fei

摘要

Abstract >We herein report a general organocatalytic enantioselective strategy for the construction of highly strained spiro[2,3]hexane skeletons from methylenecyclopropanes and a broad selection of α,β‐unsaturated aldehydes. The reaction proceeds through a Michael addition followed by ring expansion of methylenecyclopropanes and nucleophilic attack of an enamine to realize the construction of spiro[2,3]hexanes. Key to the success of this approach are the utilization of an electron‐deficient difluoro‐substituted secondary amine catalyst and the intrinsic reactivity of methylenecyclopropanes. </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> 我们在此报告了一般有机催化对甲基丙烷的高度应变螺旋血红素骨质骨质的映射策略和广泛选择的α，β-不饱和醛。反应通过迈克尔加成进行，然后进行甲基二氯丙烷环膨胀，烯胺的亲核侵蚀实现螺螺纹酸的构建。这种方法的成功的关键是利用电子不足的二氟取代的仲胺催化剂和甲基二氯丙烷的内在反应性。</ 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8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=Zhao Chuan‐Gang&option=202" target="_blank" rel="nofollow">Zhao Chuan‐Gang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Feng Zhi‐Tao&option=202" target="_blank" rel="nofollow">Feng Zhi‐Tao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu Guo‐Qiang&option=202" target="_blank" rel="nofollow">Xu Guo‐Qiang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gao Ang&option=202" target="_blank" rel="nofollow">Gao Ang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Jing‐Wei&option=202" target="_blank" rel="nofollow">Chen Jing‐Wei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Zhu‐Yin&option=202" target="_blank" rel="nofollow">Wang Zhu‐Yin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu Peng‐Fei&option=202" target="_blank" rel="nofollow">Xu Peng‐Fei;</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>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 P. R. China;</p> <p>Department of ChemistryUniversity of California-DavisOne Shields Avenue Davis CA 95616 USA;</p> <p>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 P. R. China;</p> <p>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 P. R. China;</p> <p>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 P. R. China;</p> <p>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 P. R. China;</p> <p>State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000 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=asymmetric catalysis&option=203" rel="nofollow">asymmetric catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cascade reactions&option=203" rel="nofollow">cascade reactions;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=organocatalysis&option=203" rel="nofollow">organocatalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=spirocycles&option=203" rel="nofollow">spirocycles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=synthetic methods&option=203" rel="nofollow">synthetic methods;</a> </p> <div class="translation"> 机译：不对称催化;级联反应;有机成分;螺旋形式;合成方法; </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 >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704028161970.html">Highly Enantioselective Construction of Strained Spiro[2,3]hexanes through a Michael Addition/Ring Expansion/Cyclization Cascade</a> 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