Catalytic enantioselective Passerini three-component reaction
2008
Abstract
A [(salen)-AlIIICl] complex catalyzes the Passerini three-component reaction of an aldehyde, a carboxylic acid, and an isocyanide to afford alpha -acyloxyamides, e.g., I, with good to excellent enantioselectivity. A variety of nonchelating substrates can be used to generate the versatile chiral products. [on SciFinder (R)]
Details
Title
Catalytic enantioselective Passerini three-component reaction
Author(s)
Wang, Shi-Xin ; Wang, Mei-Xiang ; Wang, De-Xian ; Zhu, Jieping
Published in
Angewandte Chemie, International Edition
Volume
47
Issue
2
Pages
388-391
Date
2008
ISSN
1433-7851
Keywords
Amides Role: SPN (Synthetic preparation); PREP (Preparation) (acyloxy-; stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes; isocyanides; and carboxylic acids); Addition reaction catalysts; Stereoselective synthesis (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes; isocyanides; and carboxylic acids); Aldehydes; Carboxylic acids; Isocyanides Role: RCT (Reactant); RACT (Reactant or reagent) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes; isocyanides; and carboxylic acids); Passerini reaction (stereoselective; stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes; isocyanides; and carboxylic acids); aldehyde isocyanide carboxylic acid salen Passerini three component reaction; amide alpha acyloxy stereoselective prepn
Note
CAN 148:331324
23-18
Aliphatic Compounds
National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6; 135616-40-9; 336105-91-0 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids); 64-19-7 (Acetic acid); 65-85-0 (Benzoic acid); 68-11-1 (Thioglycolic acid); 78-84-2 (Isobutyraldehyde); 79-11-8 (Chloroacetic acid); 79-41-4 (2-Methylacrylic acid); 104-53-0 (3-Phenylpropanal); 111-71-7 (Heptanal); 123-38-6 (Propionaldehyde); 931-54-4 (Isocyanobenzene); 1930-94-5; 2043-61-0 (Cyclohexanecarbaldehyde); 7175-47-5 (1-Isocyano-4-methylbenzene); 10340-91-7 (Benzyl isocyanide); 10349-38-9 (1-Isocyano-4-methoxybenzene); 33554-73-3; 165459-70-1 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids); 612485-86-6P; 612485-89-9P; 1011489-13-6P; 1011489-14-7P; 1011489-15-8P; 1011489-16-9P; 1011489-17-0P; 1011489-18-1P; 1011489-19-2P; 1011489-20-5P; 1011489-21-6P; 1011489-22-7P; 1011489-23-8P; 1011489-24-9P; 1011489-25-0P; 1011489-26-1P; 1011489-27-2P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids)
23-18
Aliphatic Compounds
National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry,Chinese Academy of Sciences,Beijing,Peop. Rep. China.
Journal
written in English.
96-10-6; 135616-40-9; 336105-91-0 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids); 64-19-7 (Acetic acid); 65-85-0 (Benzoic acid); 68-11-1 (Thioglycolic acid); 78-84-2 (Isobutyraldehyde); 79-11-8 (Chloroacetic acid); 79-41-4 (2-Methylacrylic acid); 104-53-0 (3-Phenylpropanal); 111-71-7 (Heptanal); 123-38-6 (Propionaldehyde); 931-54-4 (Isocyanobenzene); 1930-94-5; 2043-61-0 (Cyclohexanecarbaldehyde); 7175-47-5 (1-Isocyano-4-methylbenzene); 10340-91-7 (Benzyl isocyanide); 10349-38-9 (1-Isocyano-4-methoxybenzene); 33554-73-3; 165459-70-1 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids); 612485-86-6P; 612485-89-9P; 1011489-13-6P; 1011489-14-7P; 1011489-15-8P; 1011489-16-9P; 1011489-17-0P; 1011489-18-1P; 1011489-19-2P; 1011489-20-5P; 1011489-21-6P; 1011489-22-7P; 1011489-23-8P; 1011489-24-9P; 1011489-25-0P; 1011489-26-1P; 1011489-27-2P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of alpha -acyloxyamides via salen/Lewis acid-catalyzed Passerini three-component reaction of aldehydes, isocyanides, and carboxylic acids)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25