Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha -Addition of Isocyanides to Aldehydes
2009
Résumé
A chiral Lewis acid catalyst was prepd. by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et2AlCl. In the presence of a catalytic amt. of [I]2Al(III)Cl complex (0.05 equiv), reaction between alpha -isocyanoacetamides and aldehydes afforded the corresponding 5-aminooxazoles, e.g. II, in good yields and enantioselectivities. Complex [I]2Al(III)Cl isolated as a white solid displayed similar reactivity as that prepd. in situ. [on SciFinder (R)]
Détails
Titre
Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum-Organophosphate-Catalyzed Enantioselective alpha -Addition of Isocyanides to Aldehydes
Auteur(s)
Yue, Tao ; Wang, Mei-Xiang ; Wang, De-Xian ; Masson, Geraldine ; Zhu, Jieping
Publié dans
Journal of Organic Chemistry
Volume
74
Numéro
21
Pages
8396-8399
Date
2009
ISSN
0022-3263
Mots-clés (libres)
Aldehydes; Isocyanides Role: RCT (Reactant); RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); Passerini reaction; Passerini reaction catalysts (stereoselective; stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); organophosphate aluminum catalyst isocyanoacetamide aldehyde asym Passerini type reaction; aminooxazole stereoselective prepn
Note
CAN 151:508512
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6 (Diethylaluminum chloride); 922711-71-5 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 1192888-03-1P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 78-84-2 (Isobutanal); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 85059-38-7; 85059-48-9; 215648-69-4; 336105-88-5; 911817-35-1; 943030-28-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 951241-53-5P; 951241-54-6P; 951241-55-7P; 1192583-11-1P; 1192583-12-2P; 1192583-13-3P; 1192583-14-4P; 1192583-15-5P; 1192583-16-6P; 1192583-17-7P; 1192583-18-8P; 1192583-19-9P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes)
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6 (Diethylaluminum chloride); 922711-71-5 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 1192888-03-1P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 78-84-2 (Isobutanal); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 123-38-6 (Propanal); 85059-38-7; 85059-48-9; 215648-69-4; 336105-88-5; 911817-35-1; 943030-28-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes); 951241-53-5P; 951241-54-6P; 951241-55-7P; 1192583-11-1P; 1192583-12-2P; 1192583-13-3P; 1192583-14-4P; 1192583-15-5P; 1192583-16-6P; 1192583-17-7P; 1192583-18-8P; 1192583-19-9P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of aminooxazoles via Al-organophosphate-catalyzed asym. Passerini-type reaction of alpha -isocyanatoacetamides and aldehydes)
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