Alkoxy Radical-Triggered 1,1,2-Trifunctionalization of Unactivated Alkenes towards N,O-Spiroaminals
Min Dong , Xi Lu , Sha Yu , Zhongyu Qi , Yuanbo Yuan , Yimou Gong , Siping Wei , Xi Du , Dong Yi
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (14) : 1657 -1663.
Alkoxy Radical-Triggered 1,1,2-Trifunctionalization of Unactivated Alkenes towards N,O-Spiroaminals
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.
N,O-Spiroaminal / Trifunctionalization / Radical reactions / Vinyl azide / Coupling reaction / Photoredox catalysis / Alkoxy radical / Synthetic methods
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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