Organocatalytic Enantioselective One-Pot Four-Component Ugi-Type Multicomponent Reaction for the Synthesis of Epoxy-tetrahydropyrrolo[3,4-b]pyridin-5-ones.

Yingpeng Su (1) , Marinus J Bouma (1) , Lilian Alcaraz , Mike Stocks , Mark Furber , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

Enantioselective multicomponent reaction: In the presence of a catalytic amount of chiral BINOL-derived phosphoric acid (TRIP), the reaction of an α-isocyanoacetate 1, an aldehyde 2, and an aniline 3, followed by addition of a toluene solution of α,β-unsaturated acyl chloride 4 afforded the oxa-bridged tricycle 5 in excellent yield, diastereoselectivity, and enantioselectivity. Six chemical bonds, five stereogenic centers, and three cycles were formed in this one-pot four-component reaction.

Domaines: Chimie organique

Yingpeng Su, Marinus J Bouma, Lilian Alcaraz, Mike Stocks, Mark Furber, et al.. Organocatalytic Enantioselective One-Pot Four-Component Ugi-Type Multicomponent Reaction for the Synthesis of Epoxy-tetrahydropyrrolo[3,4-b]pyridin-5-ones.. Chemistry - A European Journal, 2012, 18 (40), pp.12624-7. ⟨10.1002/chem.201202174⟩. ⟨hal-00749802⟩