Dynamic Kinetic Resolution of Biaryl Lactones via a Chiral Bifunctional Amine Thiourea-Catalyzed Highly Atropo-enantioselective Transesterification

A solution to the unmet synthetic challenge of achieving highly atropo-enantioselective transesterification of Bringmann's lactones has been realized, employing a chiral bifunctional amine thiourea as promoter. The synergistic activation of the lactones and alcohols/phenols by the respective th...

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Published inJournal of the American Chemical Society Vol. 138; no. 22; pp. 6956 - 6959
Main Authors Yu, Chenguang, Huang, He, Li, Xiangmin, Zhang, Yueteng, Wang, Wei
Format Journal Article
LanguageEnglish
Published United States 08.06.2016
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Summary:A solution to the unmet synthetic challenge of achieving highly atropo-enantioselective transesterification of Bringmann's lactones has been realized, employing a chiral bifunctional amine thiourea as promoter. The synergistic activation of the lactones and alcohols/phenols by the respective thiourea and amine groups is crucial for achieving the highly enantioselective, high-yielding dynamic kinetic resolution process. This protocol gives highly optically pure, axially chiral biaryl compounds with a broad substrate scope under mild reaction conditions.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b03609