Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives.
The aza-MBH reaction of imines 1 and beta-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity.
Abermil
Nacim
N
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Masson
Géraldine
G
Zhu
Jieping
J
D000179:Acrylates / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D006912:Hydroxyquinolines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism
D000179:Acrylates; D001372:Aza Compounds; D006912:Hydroxyquinolines; D007097:Imines; D009281:Naphthalenes; D009284:Naphthols; D011812:Quinuclidines; C517075:beta-isocupreidine