Chiral Bronsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction

The three-component Povarov reaction of aldehydes, anilines, and benzyl N-vinylcarbamate in the presence of 0.1 equiv of chiral phosphoric acid afforded cis-2,4-disubstituted tetrahydroquinolines, e.g. I, in good yields and excellent enantiomeric excesses. The shortest synthesis of torcetrapib reported to date, which features this key three-component reaction, is documented. [on SciFinder (R)]


Published in:
Journal of the American Chemical Society, 131, 13, 4598-4599
Year:
2009
Keywords:
Amines Role: RCT (Reactant) ; RACT (Reactant or reagent) (aryl; prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); Diels-Alder reaction (aza- ; Povarov reaction; prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); Multicomponent reaction; Stereoselective synthesis (prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); Bronsted acids Role: CAT (Catalyst use) ; USES (Uses) (prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); Aldehydes Role: RCT (Reactant) ; RACT (Reactant or reagent) (prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); Diels-Alder reaction catalysts (stereoselective; prepn. of cis-2 ; 4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib) ; chiral Bronsted acid catalysis enantioselective three component Povarov reaction; cis disubstituted tetrahydroquinoline torcetrapib prepn
Note:
CAN 150:422919
27-17
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0002-7863
written in English.
1140966-34-2P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (crystal structure; prepn. of cis-2,4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); 915038-16-3P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of cis-2,4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); 62-53-3 (Aniline); 78-84-2 (Isobutanal); 95-55-6 (2-Hydroxyaniline); 98-01-1 (2-Furaldehyde); 100-52-7 (Benzaldehyde); 104-87-0 (4-Methylbenzaldehyde); 104-88-1 (4-Chlorobenzaldehyde); 104-94-9 (p-Anisidine); 105-07-7 (4-Cyanobenzaldehyde); 106-47-8 (4-Chloroaniline); 122-03-2 (4-Isopropylbenzaldehyde); 123-38-6 (Propanal); 123-72-8 (Butanal); 455-14-1 (4-(Trifluoromethyl)aniline); 455-19-6 (4-(Trifluoromethyl)benzaldehyde); 459-57-4 (4-Fluorobenzaldehyde); 541-41-3 (Ethyl chloroformate); 555-16-8 (4-Nitrobenzaldehyde); 590-86-3 (Isopentanal); 1122-91-4 (4-Bromobenzaldehyde); 3218-36-8 (4-Phenylbenzaldehyde); 32247-96-4 (3,5-Di(trifluoromethyl)benzyl bromide); 68471-57-8; 84713-20-2 (Benzyl vinylcarbamate); 152190-14-2; 915038-18-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of cis-2,4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); 474645-94-8P; 474645-96-0P; 1140966-17-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of cis-2,4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib); 262352-17-0P (Torcetrapib); 1140966-18-2P; 1140966-19-3P; 1140966-20-6P; 1140966-21-7P; 1140966-22-8P; 1140966-23-9P; 1140966-24-0P; 1140966-25-1P; 1140966-26-2P; 1140966-27-3P; 1140966-28-4P; 1140966-29-5P; 1140966-30-8P; 1140966-31-9P; 1140966-32-0P; 1140966-33-1P; 1140966-35-3P; 1140966-36-4P; 1140966-38-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of cis-2,4-disubstituted tetrahydroquinolines via chiral Bronsted acid-catalyzed enantioselective three-component Povarov reaction and synthetic application to torcetrapib)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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