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

In the presence of a catalytic amount of chiral BINOL-derived phosphoric acid (TRIP), reaction of an α-isocyanoacetate 1, an aldehyde 2, an aniline 3 followed by addition of a toluene solution of α,β-unsaturated acyl chloride 5 afforded oxa-bridged tricycle 6 in excellent yield, diastereoselectivity and enantioselectivity. Six chemical bonds, five stereogenic centers, three cycles were formed in this one pot four-component reaction.