A stepwise dearomatization/nitration/enantioselective homoenolate reaction of quinolines to construct C3-nitro-substituted tetrahydroquinolines

Abstract

Herein, we describe a stepwise 1,2-reductive dearomatization/selective C₃-nitration of quinoline and a subsequent catalytic enantioselective homoenolate addition reaction using a NHC catalyst strategy to construct N-acetyl 3,4-disubstituted tetrahydroquinoline in good yields with remarkably high diastereo- and enantioselectivities (dr >99 : 1, ee up to >99%). An efficient metal- and base-free method for 3-nitroquinoline synthesis from readily accessible quinoline has also been realized.