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. 2009 Dec 3;11(23):5546-9.
doi: 10.1021/ol9023985.

Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles

Guillaume Dagousset  1 , Fleur Drouet, Géraldine Masson, Jieping Zhu
Affiliations

Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles

Guillaume Dagousset et al. Org Lett. .

Abstract

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.

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