Alkoxy Radical-Triggered 1,1,2-Trifunctionalization of Unactivated Alkenes towards N,O-Spiroaminals

Abstract

N,O-Spiroaminals have potential biological activities and abilities to modulate the physicochemical and pharmacokinetic properties of drug molecules. However, effective catalytic methods for the efficient construction of N,O-spiroaminals are still limited to date. Herein, we report a novel 1,1,2-trifunctionalization of unactivated alkenes to rapidly and efficiently obtain a diverse array of architecturally intriguing N,O-spiroaminals. This methodology exhibits broad substrate scope, good functional group compatibility, and potential synthetic utility by a scale-up reaction, diverse product derivatizations and late-stage functionalization of complex biorelevant molecule. Notably, this transformation selectively allows for the formation of three new chemical bonds (C–O, C–C, and C–N) and one spiro quaternary carbon center across C-C double bonds.