Asymmetric synthesis of highly functionalized γ-lactams through an organocatalytic aza-Michael-Michael reaction cascade using fumaric acid amide esters as multi-reactive substrates

We developed a novel method for the asymmetric synthesis of highly functionalized gamma-lactams through an organocatalytic aza-Michael-Michael reaction cascade using fumaric acid amide esters as multi-reactive substrates. Using chiral primary or secondary amine organocatalysts, we obtained two types of gamma-lactams with three contiguous chiral centers in moderate to good yield with excellent enantioselectivity and diastereoselectivity. (C) 2012 Published by Elsevier Ltd.