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Direct Mannich‐Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts
Author(s) -
Chan Jessica Z.,
Yao Wenzhi,
Hastings Brian T.,
Lok Charles K.,
Wasa Masayuki
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608583
Subject(s) - frustrated lewis pair , chemistry , catalysis , steric effects , imine , aldimine , brønsted–lowry acid–base theory , lewis acids and bases , organocatalysis , mannich reaction , combinatorial chemistry , hydrogen bond , organic chemistry , enantioselective synthesis , molecule
Direct Mannich‐type reactions that afford both α‐ and β‐amino esters by the reaction of a broad range of carbonyl compounds and aldimines are disclosed. The transformation is promoted by a sterically frustrated Lewis acid/Brønsted base pair, which is proposed to operate cooperatively: Within the catalyst complex, an enolate is generated that then reacts with a hydrogen‐bond‐activated imine. Noncovalent interactions between reactants and the catalyst provide selectivity and new opportunities for future catalyst design.