Catalytic enantioselective Passerini three-component reaction
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)]
2008
47
2
388
391
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)
REVIEWED
OTHER