Mengwei You , Yan Li , Xin Lv , Guodong Shen , Xiao Xiao , Liejin Zhou
{"title":"Au/N-杂环卡宾中继催化下通过环异构化/[4+3]环化过程不对称合成螺呋并[2,3-b]氮杂平-5,3′-吲哚啉衍生物†","authors":"Mengwei You , Yan Li , Xin Lv , Guodong Shen , Xiao Xiao , Liejin Zhou","doi":"10.1039/d3qo00539a","DOIUrl":null,"url":null,"abstract":"<div><p>A variety of enantioenriched spirofuro[2,3-<em>b</em>]azepine-5,3′-indoline derivatives (dr > 20 : 1, up to 96% ee) were facilely synthesized through cycloisomerization/asymmetric formal [4 + 3] cycloaddition reactions of enyne-amides with isatin-derived enals under gold(<span>i</span>)/chiral N-heterocyclic carbene (NHC) relay catalysis. The method is practical and useful because of the convenient one-step procedure, high stereoselectivity, and good functional-group tolerance.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 13","pages":"Pages 3347-3352"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis†\",\"authors\":\"Mengwei You , Yan Li , Xin Lv , Guodong Shen , Xiao Xiao , Liejin Zhou\",\"doi\":\"10.1039/d3qo00539a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A variety of enantioenriched spirofuro[2,3-<em>b</em>]azepine-5,3′-indoline derivatives (dr > 20 : 1, up to 96% ee) were facilely synthesized through cycloisomerization/asymmetric formal [4 + 3] cycloaddition reactions of enyne-amides with isatin-derived enals under gold(<span>i</span>)/chiral N-heterocyclic carbene (NHC) relay catalysis. The method is practical and useful because of the convenient one-step procedure, high stereoselectivity, and good functional-group tolerance.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 13\",\"pages\":\"Pages 3347-3352\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052411023008623\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023008623","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis†
A variety of enantioenriched spirofuro[2,3-b]azepine-5,3′-indoline derivatives (dr > 20 : 1, up to 96% ee) were facilely synthesized through cycloisomerization/asymmetric formal [4 + 3] cycloaddition reactions of enyne-amides with isatin-derived enals under gold(i)/chiral N-heterocyclic carbene (NHC) relay catalysis. The method is practical and useful because of the convenient one-step procedure, high stereoselectivity, and good functional-group tolerance.
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