Jun Zhao, Xiuqi Shi, Shuo Tan, Yue Li, Ran Li, Birou Zhang, Hao Song, Fei Xue, Yong Qin
{"title":"Aporphinol-Derived Chiral Phosphoric Acids: Synthesis and Catalytic Performance","authors":"Jun Zhao, Xiuqi Shi, Shuo Tan, Yue Li, Ran Li, Birou Zhang, Hao Song, Fei Xue, Yong Qin","doi":"10.1021/acs.orglett.5c00940","DOIUrl":null,"url":null,"abstract":"A novel series of chiral phosphoric acid (CPA) catalysts based on a bioinspired aporphinol scaffold has been developed. The efficacy of these CPAs is demonstrated through enantioselective transfer hydrogenation of C2-substituted quinolines, achieving excellent enantioselectivities (93–99% enantiomeric excess). They also exhibit catalytic efficiency comparable to that of classic chiral phosphoric acids in the asymmetric Friedel–Crafts reaction and reduction of ketone. This work highlights the potential of aporphinol-based catalysts for diverse asymmetric transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-04-18","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.5c00940","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 novel series of chiral phosphoric acid (CPA) catalysts based on a bioinspired aporphinol scaffold has been developed. The efficacy of these CPAs is demonstrated through enantioselective transfer hydrogenation of C2-substituted quinolines, achieving excellent enantioselectivities (93–99% enantiomeric excess). They also exhibit catalytic efficiency comparable to that of classic chiral phosphoric acids in the asymmetric Friedel–Crafts reaction and reduction of ketone. This work highlights the potential of aporphinol-based catalysts for diverse asymmetric transformations.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
