N‐Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Pentacyclic Spirooxindoles via [3+3] Annulations of Isatin‐Derived Enals and Cyclic N‐Sulfonyl Ketimines

Liu Qiang; Chen Xiang‐Yu; Li Sun; Rissanen Kari; Enders Dieter

摘要

Abstract >A convenient enantioselective route to new types of pentacyclic spirooxindoles via [3+3] annulation reactions of isatin‐derived enals and cyclic N‐sulfonyl ketimines, using N‐heterocyclic carbene (NHC) catalysis has been developed. The new protocol leads to pentacyclic spirooxindoles bearing a quaternary spiro‐stereocenter in good yields and good to high enantiomeric ratios. > <blockFixed type="graphic"> <mediaResourceGroup> <mediaResource alt="image" href="urn:x-wiley:16154150:media:adsc201900065:adsc201900065-toc-0001"/> </mediaResourceGroup> </blockFixed> </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> 已经开发了通过[3 + 3]衍生的烯醇和环状N-磺酰基亚胺的新型戊基螺氧吲哚吲哚酮的新类型的戊氰基吲哚，使用N-杂环碳（NHC）催化的方便映射途径。新的方案导致五环素螺氧吲哚吲哚，血液螺旋形超中心，良好的产量和高对映体比率。</ p> > <blockfixed type =“图形”> <mediaresourcegroup> <MediareSource Alt =“image”Href =“URN：X-Wiley：16154150：媒体：ADSC201900065：ADSC201900065-TOC-0001”/> </ mediaresourcegroup> </ blockfixed> </ 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-19407/'>《Advanced synthesis & catalysis》</a> <b style="margin: 0 2px;">|</b><span>2019年第9期</span><b style="margin: 0 2px;">|</b><span>共4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=Liu Qiang&option=202" target="_blank" rel="nofollow">Liu Qiang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Xiang‐Yu&option=202" target="_blank" rel="nofollow">Chen Xiang‐Yu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Sun&option=202" target="_blank" rel="nofollow">Li Sun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Rissanen Kari&option=202" target="_blank" rel="nofollow">Rissanen Kari;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Enders Dieter&option=202" target="_blank" rel="nofollow">Enders Dieter;</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>Institute of Organic ChemistryRWTH Aachen UniversityAachen 52074 Germany;</p> <p>Institute of Organic ChemistryRWTH Aachen UniversityAachen 52074 Germany;</p> <p>Institute of Organic ChemistryRWTH Aachen UniversityAachen 52074 Germany;</p> <p>Department of ChemistryUniversity ofJyvaskyla P. O. Box 35 40014 Jyv?skyl? Finland;</p> <p>Institute of Organic ChemistryRWTH Aachen UniversityAachen 52074 Germany;</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/238.html" title="化学工业">化学工业;</a><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a><a href="https://www.zhangqiaokeyan.com/clc/7777.html" title="化学反应过程">化学反应过程;</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=pentacyclic spirooxindoles&option=203" rel="nofollow">pentacyclic spirooxindoles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=N-heterocyclic carbenes&option=203" rel="nofollow">N-heterocyclic carbenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=isatin-derived enals&option=203" rel="nofollow">isatin-derived enals;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cyclic ketimines&option=203" rel="nofollow">cyclic ketimines;</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> </p> <div class="translation"> 机译：五环素螺氧吲哚;正杂环碳;isatin衍生的enals;循环酮段;不对称合成; </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" 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