Chiral Bronsted Acid-Catalyzed Enantioselective Multicomponent Mannich Reaction: Synthesis of anti-1,3-Diamines Using Enecarbamates as Nucleophiles

Reaction of aldehydes, anilines, and enecarbamates in dichloromethane in the presence of EtOH and a catalytic amt. of chiral phosphoric acid I afforded the Mannich adducts which were in situ reduced to anti-1,2-disubstituted 1,3-diamines II in excellent diastereoselectivity and enantioselectivity. [on SciFinder (R)]


Published in:
Organic Letters, 11, 23, 5546-5549
Year:
2009
Keywords:
Note:
CAN 152:11611
21-2
General Organic Chemistry
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
1140966-18-2P; 1140966-33-1P Role: BYP (Byproduct), PREP (Preparation) (prepn. of anti-diamines via chiral Bronsted acid-catalyzed multicomponent Mannich reaction of aldehydes, anilines, and enecarbamates); 915038-16-3P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of anti-diamines via chiral Bronsted acid-catalyzed multicomponent Mannich reaction of aldehydes, anilines, and enecarbamates); 62-53-3 (Aniline); 78-84-2 (Isobutanal); 98-01-1 (2-Furfural); 100-01-6; 100-52-7 (Benzaldehyde); 104-53-0 (Hydrocinnamaldehyde); 104-94-9 (4-Methoxyaniline); 106-47-8 (4-Chloroaniline); 123-11-5 (p-Anisaldehyde); 123-38-6 (Propanal); 1122-91-4 (4-Bromobenzaldehyde); 3218-36-8 ([1,1'-Biphenyl]-4-carboxaldehyde); 6630-33-7 (2-Bromobenzaldehyde); 7150-72-3 (tert-Butyl N-vinylcarbamate); 14371-10-9 ((E)-Cinnamaldehyde); 60656-87-3 (2-(Benzyloxy)acetaldehyde); 84713-20-2 (Benzyl N-vinylcarbamate); 260967-06-4; 260967-14-4; 915038-18-5; 1197815-61-4 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of anti-diamines via chiral Bronsted acid-catalyzed multicomponent Mannich reaction of aldehydes, anilines, and enecarbamates); 1197815-33-0P; 1197815-34-1P; 1197815-35-2P; 1197815-36-3P; 1197815-37-4P; 1197815-38-5P; 1197815-49-8P; 1197815-63-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of anti-diamines via chiral Bronsted acid-catalyzed multicomponent Mannich reaction of aldehydes, anilines, and enecarbamates); 1140966-34-2P; 1197815-39-6P; 1197815-40-9P; 1197815-41-0P; 1197815-42-1P; 1197815-43-2P; 1197815-44-3P; 1197815-45-4P; 1197815-46-5P; 1197815-47-6P; 1197815-48-7P; 1197815-50-1P; 1197815-51-2P; 1197815-52-3P; 1197815-53-4P; 1197815-54-5P; 1197815-55-6P; 1197815-56-7P; 1197815-57-8P; 1197815-58-9P; 1197815-59-0P; 1197815-60-3P; 1197815-62-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of anti-diamines via chiral Bronsted acid-catalyzed multicomponent Mannich reaction of aldehydes, anilines, and enecarbamates)
Laboratories:




 Record created 2010-11-25, last modified 2018-01-28


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