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. 2017 Oct 16;56(43):13338-13341.
doi: 10.1002/anie.201708103. Epub 2017 Sep 22.

Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes

Ming Shang  1 , Min Cao  1 , Qifan Wang  1 , Masayuki Wasa  1
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Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes

Ming Shang et al. Angew Chem Int Ed Engl. .

Abstract

An enantioselective direct Mannich-type reaction catalyzed by a sterically frustrated Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the chiral Lewis acid and achiral Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reaction with hydrogen-bond-activated aldimines delivers β-aminocarbonyl compounds with high enantiomeric purity.

Keywords: Lewis acids; Mannich reactions; acid/base catalysis; boron; frustrated Lewis pairs.

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