{"title":"2-氨基-3取代吲哚的有机催化立体发散脱芳化和n -酰化","authors":"Lunfeng Chen, Pengfei Li","doi":"10.1021/acs.orglett.4c04164","DOIUrl":null,"url":null,"abstract":"Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34–79% yields with 61–91% ee. With Boc<sub>2</sub>O as reaction partner, the organocatalytic enantioselective <i>N</i>-acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22–98% yields with 73–92% ee.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"215 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles\",\"authors\":\"Lunfeng Chen, Pengfei Li\",\"doi\":\"10.1021/acs.orglett.4c04164\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34–79% yields with 61–91% ee. With Boc<sub>2</sub>O as reaction partner, the organocatalytic enantioselective <i>N</i>-acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22–98% yields with 73–92% ee.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"215 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2024-12-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c04164\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04164","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles
Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34–79% yields with 61–91% ee. With Boc2O as reaction partner, the organocatalytic enantioselective N-acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22–98% yields with 73–92% ee.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.