Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst

Abstract

Herein, the aldol/Michael cascade reaction on the β,γ-positions of α,β-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates were well-tolerated with high regio- and diastereoselectivities in moderate to good yields (32 examples). The control experiments revealed that the hydrogen of the amide was the key factor.