Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds

Abstract

A chiral anthranilic pyrrolidine catalyst as a custom-made amine-catalyst was developed for the enantio- and diastereo selective Michael reaction of nitroalkenes with carbonyl compounds. In particular, a peptide-like catalyst in which an α-amino acid is attached to the anthranilic acid skeleton induced the high stereoselectivity of the reaction with aldehydes. Studies of the reaction mechanism indicated that the catalyst exhibits a divergent stereocontrol in the reaction, namely, steric control by a 2-substituted group on the catalyst and hydrogen-bonding control by a carboxylic acid group on the catalyst.