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

Research output: Contribution to journalArticlepeer-review

95 Scopus citations

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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