Hui Wang, Xian-Qing Peng, Yang Yang, Ze-Xiang Geng, Bo-Lin Sun, Ling Zhou, Jie Chen
{"title":"Construction of Axially Chiral 4-Aminoquinolines by Cycloaddition and Central-to-Axial Chirality Conversion","authors":"Hui Wang, Xian-Qing Peng, Yang Yang, Ze-Xiang Geng, Bo-Lin Sun, Ling Zhou, Jie Chen","doi":"10.1021/acs.orglett.4c03827","DOIUrl":null,"url":null,"abstract":"A two-step strategy has been established for the enantioselective synthesis of 4-aminoquinolines possessing axial chirality. This approach involves a chiral phosphoric acid-catalyzed cycloaddition, followed by a DDQ oxidation step. The method offers efficient access to a variety of 1,1′-biaryl-2,2′-amino alcohol derivatives in excellent yields and enantioselectivities (up to 98% yield and 93% ee). Furthermore, the synthetic transformation of the products was also investigated.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-14","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.4c03827","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A two-step strategy has been established for the enantioselective synthesis of 4-aminoquinolines possessing axial chirality. This approach involves a chiral phosphoric acid-catalyzed cycloaddition, followed by a DDQ oxidation step. The method offers efficient access to a variety of 1,1′-biaryl-2,2′-amino alcohol derivatives in excellent yields and enantioselectivities (up to 98% yield and 93% ee). Furthermore, the synthetic transformation of the products was also investigated.
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.