Pseudo‐Stereodivergent Synthesis of Enantioenriched Tetrasubstituted Alkenes by Cascade 1,3‐Oxo‐Allylation/Cope Rearrangement

Chen Peng; Li Yue; Chen Zhi‐Chao; Du Wei; Chen Ying‐Chun

摘要

Abstract > The catalytic diastereodivergent construction of stereoisomers having two or more stereogenic centers has been extensively studied. In contrast, the switchable introduction of another stereogenic element, that is, Z / E configuration involving a polysubstituted alkene group, into the optically active stereoisomers, has not been recognized yet. Disclosed here is the pseudo‐stereodivergent synthesis of highly enantioenriched tetrasubstituted alkene architectures from isatin‐based Morita–Baylis–Hillman carbonates and allylic derivatives, under the cooperative catalysis of a tertiary amine and a chiral iridium complex. The success of the switchable construction of the tetrasubstituted alkene motif relies on the diastereodivergent 1,3‐oxo‐allylation reaction between N‐allylic ylides and chiral π‐allyliridium complex intermediates by ligand and substrate control, followed by the stereoselective concerted 3,3‐Cope rearrangement process. </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> > 已经广泛研究了具有两个或更多个立体中心的立体异构体的催化解除映异构体。相比之下，另一种立体元素的可切换引入，即 z </ i> / e </ i> 涉及多助化烯烃基团进入光学活性立体异构体的构型尚未得到识别。这里公开了来自Isatin的莫提塔 - 巴利斯 - 丘比特 - 纳米碳酸酯和烯丙基衍生物的伪立体烯酮烯烃架构的伪静态化合成，在叔胺和手性铱络合物的协同催化下。通过配体和底物对照依赖于N-烯丙基杯和手性π-烯丙啶络合物中间体之间的乳糖和π-烯丙基复合体之间的非对映号的1,3-氧基烯丙基化反应的可切换结构的成功。应对重新排列过程。 </ 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18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=Chen Peng&option=202" target="_blank" rel="nofollow">Chen Peng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Yue&option=202" target="_blank" rel="nofollow">Li Yue;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Zhi‐Chao&option=202" target="_blank" rel="nofollow">Chen Zhi‐Chao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Du Wei&option=202" target="_blank" rel="nofollow">Du Wei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Ying‐Chun&option=202" target="_blank" rel="nofollow">Chen Ying‐Chun;</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>Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial TechnologySichuan UniversityChengdu 610041 China;</p> <p>Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial TechnologySichuan UniversityChengdu 610041 China;</p> <p>Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial TechnologySichuan UniversityChengdu 610041 China;</p> <p>Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial TechnologySichuan UniversityChengdu 610041 China;</p> <p>Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial TechnologySichuan UniversityChengdu 610041 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=alkenes&option=203" rel="nofollow">alkenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=allylic compounds&option=203" rel="nofollow">allylic compounds;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cooperative catalysis&option=203" rel="nofollow">cooperative catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=iridium&option=203" rel="nofollow">iridium;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=rearrangements&option=203" rel="nofollow">rearrangements;</a> </p> <div class="translation"> 机译：alkenes;烯丙基化合物;合作催化;铱;重排; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" 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class="tuijian_auth tuijian_authcolor">,殷建国</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐维铧&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐维铧</a> <span> <a href="/journal-cn-53859/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学学报 </a> </span> <span> . 1990</span><span>,第2期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-65534_thesis/020222947815.html">一种烯丙基聚氧烯环氧基醚的合成</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=杨振声&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 杨振声</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张磊&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张磊</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=秦丽翠&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,秦丽翠</a> <span> <a href="/conference-cn-65534/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . “润禾杯”浙江省纺织印染助剂行业第27届学术年会 </a> <span> <span> . 2017</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311598416.html">锡粉促进下的醛、2-亚氨基异吲哚啉-1,3-二酮、烯丙基溴合成高烯丙基酰肼类化合物反应研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ABDALHLIM HAFIZ&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . ABDALHLIM HAFIZ</a> <span> . 2017</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105207088.html">包括1,3－二氧杂环己－5－酮的烯胺与硝基烯烃之间反应的多氧代氮体系合成</a> <b>[P]</b> . <span> 中国专利： CN101006071A </span> <span> . 2007-07-25</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061204491720.html">一种烯烃1,4-双官能团化反应制备烯丙基吲哚类化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN108912036B </span> <span> . 2021.06.25</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130412287889.html">Route to synthetic analogues of Rocaglamide and Aglafoline using cascade transformations initiated by oxy-cope rearrangement of bis-alkynes</a> <b>[P]</b> . <span> 外国专利：  US9206100B2 </span> <span> . 2015-12-08</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：使用由双炔烃的氧应付重排引发的级联转化途径合成Rocaglamide和Aglafoline的合成类似物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130420840968.html">NEW ROUTE TO SYNTHETIC ANALOGUES OF ROCAGLAMIDE AND AGLAFOLINE USING CASCADE TRANSFORMATIONS INITIATED BY OXY-COPE REARRANGEMENT OF BIS-ALKYNES</a> <b>[P]</b> . <span> 外国专利：  US2013165683A1 </span> <span> . 2013-06-27</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：双链炔烃的氧-杯配位引发的级联转化，合成了洛克卡酰胺和阿格福林合成类似物的新途径 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130422475757.html">NEW ROUTE TO SYNTHETIC ANALOGUES OF ROCAGLAMIDE AND AGLAFOLINE USING CASCADE TRANSFORMATIONS INITIATED BY OXY-COPE REARRANGEMENTS OF BIS-ALKYNES</a> <b>[P]</b> . <span> 外国专利：  WO2012037062A3 </span> <span> . 2012-05-18</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：双链炔烃的氧-杯重整引发的级联转化，合成了洛卡酰胺和阿格福林类似物的新路线 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028161118','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> <h2>期刊订阅</h2> <img src="https://cdn.zhangqiaokeyan.com/img/loginclose.png" alt="关闭" onclick="$('.journalsub-pop-up').hide()"> <p class="pardon">抱歉，该期刊暂不可订阅，敬请期待！</p> <p 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