Abermil, NacimMasson, GeraldineZhu, Jieping2010-11-252010-11-252010-11-25200910.1021/ol901920shttps://infoscience.epfl.ch/handle/20.500.14299/58408The 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)]Baylis-Hillman reaction; Baylis-Hillman reaction catalysts; Reaction mechanism; Stereoselective synthesis (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Sulfonamides Role: SPN (Synthetic preparation)PREP (Preparation) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Imides; Sulfonic acids Role: RCT (Reactant)RACT (Reactant or reagent) (sulfonimides; invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Ketones Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (alphabeta -unsatd.; invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones)sulfonyl allylamide asym prepn; sulfonylimine vinyl ketone asym aza Morita Baylis Hillman addn; acylamino isocupreidine catalyst naphthol achiral additive invertible enantioselectivity mechanismtext::journal::journal article::research article