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

Guillaume Dagousset , Fleur Drouet , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

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.

Domaines: Biologie cellulaire

Guillaume Dagousset, Fleur Drouet, Géraldine Masson, Jieping Zhu. Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles.. Organic Letters, 2009, 11 (23), pp.5546-9. ⟨10.1021/ol9023985⟩. ⟨hal-00451493⟩