Synfacts 2010(1): 0110-0110  
DOI: 10.1055/s-0029-1218495
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Cascade Reactions of Amphoteric Amino Aldehydes

Contributor(s): Benjamin List, Anna Lee
R. Hili, A. K. Yudin*
University of Toronto, Canada
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

An unusual Baylis-Hillman reac-tion of amphoteric amino aldehydes via an aza-­Michael-aldol cascade is reported. Using a secondary amine-Brønsted acid catalyst combination, the authors obtained compounds 1. The use of aprotic solvents which slow down the dissociation of dimer 2 was crucial. The proposed mechanism begins with the activation of α,β-unsaturated aldehyde by iminium catalysis. This electrophile initiates a domino process within the amphoteric molecule leading to products 1.