Lithium alkoxide-promoted Michael reaction between silyl enolates and α,β-unsaturated carbonyl compounds

Michael reaction between silyl enolates and alpha,beta-unsaturated carbonyl compounds by using a catalytic amount of Lewis base such as lithium alkoxide in DMF proceeds smoothly to afford the corresponding Michael-adducts in good yields with moderate to high diastereoselectivities. This reaction can be reasonably explained by considering an alkoxide anion-initiated autocatalytic process.