Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts

Autor:	Brian T. Hastings, Masayuki Wasa, Wenzhi Yao, Charles K. Lok, Jessica Z. Chan
Rok vydání:	2016
Předmět:	chemistry.chemical_classification Steric effects Aldimine Chemistry 010405 organic chemistry Imine General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Frustrated Lewis pair 0104 chemical sciences chemistry.chemical_compound Non-covalent interactions Organic chemistry Lewis acids and bases Brønsted–Lowry acid–base theory
Zdroj:	Angewandte Chemie. 128:14081-14085
ISSN:	0044-8249
DOI:	10.1002/ange.201608583
Popis:	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.
Databáze:	OpenAIRE
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