An organocatalytic enantioselective ring-reorganization domino sequence of methyleneindolinones with 2-aminomalonates

Abstract

An organocatalytic enantioselective ring-reorganization domino sequence (Michael addition/intramolecular ring-opening/lactamization) of methyleneindolinones with 2-aminomalonates has been established in this work. As a result, pyrrolo[3,4-c]quinolinones bearing two to three contiguous chiral centers were efficiently assembled in high yields (up to 92%) with excellent diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to >99% ee).