Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 44, Pages 13877-13881Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608583
Keywords
acid-base catalysis; boron; frustrated Lewis pairs; Lewis acids; Mannich-type reactions
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Funding
- Boston College
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Direct Mannich-type reactions that afford both aand beta-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/Bronsted 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.
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