title: Dynamic Kinetic Resolution of Biaryl Lactones via a Chiral Bifunctional Amine Thiourea-Catalyzed Highly Atropo-enantioselective Transesterification.
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.
authors.affiliation: Department of Chemistry & Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States.
authors.forename: Chenguang
authors.initials: C
authors.lastname: Yu
authors.affiliation: Department of Chemistry & Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States.
authors.forename: He
authors.initials: H
authors.lastname: Huang
authors.affiliation: Department of Chemistry & Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States.|Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactor, East China University of Science & Technology , Shanghai 200237, China.
authors.forename: Xiangmin
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Chemistry & Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States.
authors.forename: Yueteng
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry & Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States.|Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactor, East China University of Science & Technology , Shanghai 200237, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
mesh_terms: D000588:Amines / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004951:Esterification; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000588:Amines; D001555:Benzene Derivatives; D007783:Lactones; D013890:Thiourea