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

Herein, the aldol/Michael cascade reaction on the beta,gamma-positions of alpha,beta-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.

Automated summary

In this study, a aldol/Michael cascade reaction on the beta,gamma-positions of alpha,beta-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates exhibited high regio- and diastereoselectivities and yielded moderate to good results (32 examples). Control experiments showed that the hydrogen of the amide played a key role.