Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles.
Reaction of aldehydes 2, anilines 3, and enecarbamates 4 in dichloromethane in the presence of EtOH and a catalytic amount of chiral phosphoric acid 5 afforded the Mannich adducts which were in situ reduced to anti-1,2-disubstituted 1,3-diamines 1 in excellent diastereoselectivity and enantioselectivity.
Dagousset
Guillaume
G
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Drouet
Fleur
F
Masson
Géraldine
G
Zhu
Jieping
J
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003959:Diamines