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Copper‐Catalyzed Enantioselective 1,6‐Boration of para ‐Quinone Methides and Efficient Transformation of gem ‐Diarylmethine Boronates to Triarylmethanes
Author(s) -
Lou Yazhou,
Cao Peng,
Jia Tao,
Zhang Yongling,
Wang Min,
Liao Jian
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505926
Subject(s) - enantioselective synthesis , chemistry , catalysis , conjugate , quinone , copper , combinatorial chemistry , transformation (genetics) , organic chemistry , mathematical analysis , biochemistry , mathematics , gene
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.