Invertible Enantioselectivity in 6'-Deoxy-6'-acylamino-beta -isocupreidine-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction: Key Role of Achiral Additive

The beta -isocupreidine (beta -ICD) or beta -ICD-amide (I)-catalyzed aza-Morita-Baylis-Hillman reaction between N-sulfonylimines and alkyl vinyl ketones produced the (R)-enriched adducts, e.g. II. By adding a catalytic amt. of beta -naphthol, the enantioselectivity of the same reaction was inversed leading to (S)-isomers in excellent yields and enantioselectivities. Both arom. and aliph. imines are accepted as substrates for this reaction. [on SciFinder (R)]