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

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• 作者：Chenguang Yu ; He Huang ; Xiangmin Li ; Yueteng Zhang ; Wei Wang
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：June 8, 2016
• 年：2016
• 卷：138
• 期：22
• 页码：6956-6959
• 全文大小：451K
• 年卷期：0
• ISSN：1520-5126

文摘

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.