Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed by Bifunctional beta -Isocupreidine Derivatives
The aza-MBH reaction of imines, e.g., I, and beta -naphthyl acrylate in the presence of C-6' modified beta -isocupreidine deriv. (0.1 equiv) and beta -naphthol (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts, e.g., II, in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliph. 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 obsd. high enantioselectivity. [on SciFinder (R)]
2008
130
38
12596
12597
CAN 149:355419
23-17
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
253430-48-7; 890043-55-7 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056903-96-8P Role: CAT (Catalyst use), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), USES (Uses), RACT (Reactant or reagent) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056903-97-9P; 1056903-98-0P; 1056903-99-1P; 1056904-00-7P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 23165-29-9; 35150-06-2; 35150-09-5; 52684-34-1 (beta -Naphthyl acrylate); 52960-60-8; 52960-63-1; 129095-62-1; 612063-38-4; 656835-59-5; 656835-60-8; 890043-99-9; 1056904-01-8; 1056904-02-9; 1056904-03-0; 1056904-04-1; 1056904-05-2; 1056904-06-3; 1056904-07-4; 1056904-08-5; 1056904-09-6; 1056904-10-9; 1056904-11-0 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056904-12-1P; 1056904-13-2P; 1056904-14-3P; 1056904-15-4P; 1056904-16-5P; 1056904-17-6P; 1056904-18-7P; 1056904-19-8P; 1056904-20-1P; 1056904-21-2P; 1056904-22-3P; 1056904-23-4P; 1056904-24-5P; 1056904-25-6P; 1056904-26-7P; 1056904-27-8P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate)
REVIEWED
OTHER