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

The bifunctional catalyst 6'-deoxy-6'-acylamino-beta -isocupreidine 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 compds., e.g. I, difficultly accessible previously, can now be synthesized in excellent yields and enantioselectivity. [on SciFinder (R)]