Stereoselective Synthesis of <i>C‐</i>Vinyl Glycosides via Nickel‐Catalyzed Cross‐Electrophile Couplings of 1,2‐Glycosyl Orthoesters and Vinyl Halides
Xin Wang, Anrong Chen, Shiyin Zhao, Qiang Tao, Bo Yang, Xing Zhang, Feng Zhu
Abstract
Comprehensive Summary 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.
Topics & Concepts
ChemistryStereoselectivityGlycosylElectrophileCombinatorial chemistryCatalysisNickelHalideOrganic chemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions