Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts.
- Resource Type
- Article
- Authors
- Chan, Jessica Z.; Yao, Wenzhi; Hastings, Brian T.; Lok, Charles K.; Wasa, Masayuki
- Source
- Angewandte Chemie. 10/24/2016, Vol. 128 Issue 44, p14081-14085. 5p.
- Subject
- *LEWIS acids
*BRONSTED acids
*CARBONYL compounds
*HYDROGEN bonding
*ENOLATES
- Language
- ISSN
- 0044-8249
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. [ABSTRACT FROM AUTHOR]