Enantioselective Aza-Morita-Baylis-Hillman Reaction Using Aliphatic alpha-Amidosulfones as Imine Surrogates

The bifunctional catalyst 6'-deoxy-6'-acylamino-beta-isocupreidine (1) served both as a base to trigger the in situ generation of N-sulfonylimine from readily available alpha-amidosulfones and as a chiral nucleophile to initiate the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction. alpha-Methylene-beta-amino-beta-alkyl carbonyl compounds, difficultly accessible previously, can now be synthesized in excellent yields and enantioselectivities.