Invertible enantioselectivity in 6'-deoxy-6'-acylamino-beta-isocupreidine-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction: key role of achiral additive.
The beta-ICD (1a) or beta-ICD-amide (1e)-catalyzed aza-Morita-Baylis-Hillman reaction between N-sulfonylimines 3 and alkyl vinyl ketones 4 produced the (R)-enriched adducts 5. By adding a catalytic amount of beta-naphthol (2a), the enantioselectivity of the same reaction was inversed leading to (S)-5 in excellent yields and enantioselectivities. Both aromatic and aliphatic imines are accepted as substrates for this reaction.
Abermil
Nacim
N
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Masson
Géraldine
G
Zhu
Jieping
J
D000577:Amides / Q000737:chemistry; D002384:Catalysis; D011803:Quinine / Q000031:analogs & derivatives* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000577:Amides; D011804:Quinolines; D011812:Quinuclidines; C029819:6'-hydroxycinchonidine; D011803:Quinine