Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed by Bifunctional beta -Isocupreidine Derivatives
2008
Résumé
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)]
Détails
Titre
Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed by Bifunctional beta -Isocupreidine Derivatives
Auteur(s)
Abermil, Nacim ; Masson, Geraldine ; Zhu, Jieping
Publié dans
Journal of the American Chemical Society
Volume
130
Numéro
38
Pages
12596-12597
Date
2008
ISSN
0002-7863
Mots-clés (libres)
Imines Role: RCT (Reactant); RACT (Reactant or reagent) (aldimines; 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); Amino acids Role: SPN (Synthetic preparation); PREP (Preparation) (esters; alpha -methylene; 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); Baylis-Hillman reaction (stereoselective aza; 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); Stereoselective synthesis (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); Alkaloids 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); Addition reaction catalysts (stereoselective; Baylis-Hillman; 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); imine acrylate isocupreidine enantioselective aza Morita Baylis Hillman; amino methylene carboxylic ester stereoselective prepn; enantioselective aza Morita Baylis Hillman catalyst isocupreidine
Note
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)
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)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
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Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25