Binhong Tan , Junjie Meng , Qianru Liu , Shixin Chen , Mingyue Xue , Yue Zhang , Yuping Zhang , Zhaodong Li
{"title":"钯(II)催化氧三环烯烃与烷基苯胺的对映选择性去对称开环:对映富集功能化环己烯的有效途径","authors":"Binhong Tan , Junjie Meng , Qianru Liu , Shixin Chen , Mingyue Xue , Yue Zhang , Yuping Zhang , Zhaodong Li","doi":"10.1039/d5qo00118h","DOIUrl":null,"url":null,"abstract":"<div><div>We disclose herein a practical enantioselective desymmetrization ring-opening coupling of oxabicyclic alkenes with alkynylanilines, enabled by Pd(<span>ii</span>)-catalyzed aminopalladation cascade, allowing efficient access to a diverse set of indolated cyclohexenes bearing four contiguous densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Representative post-transformations to other valuable enantioenriched functionalized cyclohexene derivatives demonstrate the synthetic potential of this methodology.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3841-3847"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium(ii)-catalyzed enantioselective desymmetrization ring opening of oxabicyclic alkenes with alkynylanilines: efficient access to enantioenriched functionalized cyclohexenes†\",\"authors\":\"Binhong Tan , Junjie Meng , Qianru Liu , Shixin Chen , Mingyue Xue , Yue Zhang , Yuping Zhang , Zhaodong Li\",\"doi\":\"10.1039/d5qo00118h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We disclose herein a practical enantioselective desymmetrization ring-opening coupling of oxabicyclic alkenes with alkynylanilines, enabled by Pd(<span>ii</span>)-catalyzed aminopalladation cascade, allowing efficient access to a diverse set of indolated cyclohexenes bearing four contiguous densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Representative post-transformations to other valuable enantioenriched functionalized cyclohexene derivatives demonstrate the synthetic potential of this methodology.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 13\",\"pages\":\"Pages 3841-3847\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-03-28\",\"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/S2052412925002189\",\"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/S2052412925002189","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Palladium(ii)-catalyzed enantioselective desymmetrization ring opening of oxabicyclic alkenes with alkynylanilines: efficient access to enantioenriched functionalized cyclohexenes†
We disclose herein a practical enantioselective desymmetrization ring-opening coupling of oxabicyclic alkenes with alkynylanilines, enabled by Pd(ii)-catalyzed aminopalladation cascade, allowing efficient access to a diverse set of indolated cyclohexenes bearing four contiguous densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Representative post-transformations to other valuable enantioenriched functionalized cyclohexene derivatives demonstrate the synthetic potential of this methodology.