Stereoselective Synthesis of C-Vinyl Glycosides via Nickel-Catalyzed Cross-Electrophile Couplings of 1,2-Glycosyl Orthoesters and Vinyl Halides

Abstract

A highly stereoselective nickel-catalyzed cross-electrophile coupling of readily accessible, novel, stable oxygen-based glycosyl radical precursors, specifically 1,2-glycosyl orthoesters, is developed. This approach offers an effective pathway to synthesize diverse C-vinyl glycosides, characterized by good yields, excellent stereoselectivity, mild reaction conditions, a broad substrate scope, and versatile transformations of the resulting products.