title: Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes.
abstract: Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium trifluoroborates into triarylmethanes with highly enantiospecificity was realized.
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China).|University of Chinese Academy of Sciences, Beijing 100049 (China).
authors.forename: Yazhou
authors.initials: Y
authors.lastname: Lou
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China).|University of Chinese Academy of Sciences, Beijing 100049 (China).
authors.forename: Peng
authors.initials: P
authors.lastname: Cao
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China).|University of Chinese Academy of Sciences, Beijing 100049 (China).
authors.forename: Tao
authors.initials: T
authors.lastname: Jia
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China).|University of Chinese Academy of Sciences, Beijing 100049 (China).
authors.forename: Yongling
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China).|University of Chinese Academy of Sciences, Beijing 100049 (China).
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China). jliao@cib.ac.cn.|University of Chinese Academy of Sciences, Beijing 100049 (China). jliao@cib.ac.cn.|College of Chemical Engineering, Sichuan University, Chengdu 610065 (China). jliao@cib.ac.cn.
authors.forename: Jian
authors.initials: J
authors.lastname: Liao
mesh_terms: D001895:Boron / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D045563:Indolequinones / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D045563:Indolequinones; C068040:quinone methide; D003300:Copper; D001895:Boron
keywords: asymmetric catalysis; boron; copper; cross-coupling; synthetic methods