Direct Mannich‐Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts. (30th September 2016)

• Record Type: Journal Article
• Authors: Chan, Jessica Z.; Yao, Wenzhi; Hastings, Brian T.; Lok, Charles K.; Wasa, Masayuki
• Is Part Of: Angewandte Chemie. Volume 128:Number 44(2016)
• Page Start: 14081
• Page End: 14085
• Publication Date: 2016-09-30
• Subjects: Bor -- Frustrierte Lewis-Paare -- Lewis-Säuren -- Mannich-Reaktionen -- Säure-Base-Katalyse; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201608583
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.