Organocatalytic enantioselective one-pot four-component Ugi-type multicomponent reaction for the synthesis of epoxy-tetrahydropyrrolo[3,4-b] pyridin-5-ones

摘要

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.