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

Chenguang Yu, He Huang, Xiangmin Li, Yueteng Zhang, Wei Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

140 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6956-6959
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number22
DOIs
Publication statusPublished - 8 Jun 2016
Externally publishedYes

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