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Catalytic Asymmetric Disulfuration by a Chiral Bulky Three‐Component Lewis Acid‐Base
Author(s) -
Zhang Qi,
Li Yao,
Zhang Long,
Luo Sanzhong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101569
Subject(s) - enamine , lewis acids and bases , chemistry , enantioselective synthesis , frustrated lewis pair , borane , catalysis , amine gas treating , lewis acid catalysis , tertiary amine , diamine , organocatalysis , organic chemistry , polymer chemistry , medicinal chemistry
A three‐component Lewis acid–base (Lewis trio) involving a bulky chiral primary amine, B(C 6 F 5 ) 3 and a bulky tertiary amine has been developed as an effective enamine catalyst for enantioselective disulfuration reactions. The bulky tertiary amine was found to activate a bulky primary–tertiary diamine–borane Lewis pair for enamine catalysis via frustrated interaction. The resulted chiral bulky Lewis trio (BLT) allows for the construction of chiral disulfides via direct disulfuration with β‐ketocarbonyls or α‐branched aldehydes in a practical and highly stereocontrolled manner.