Lithium Alkoxide-promoted Michael Reaction between Silyl Enolates and (alpha),(beta)-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.