Stereoselective Synthesis of C-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

doi:10.1002/cjoc.202400651

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (23) : 3029 -3034. DOI: 10.1002/cjoc.202400651

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

Xin Wang ¹^,²^,³
, Anrong Chen ³
, Shiyin Zhao ³
, Qiang Tao ²^,³
, Bo Yang ³^,^†
, Xing Zhang ²^,^†
, Feng Zhu ¹^,³^,^†

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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.

Keywords

Glycosylation / Nickel catalysis / Cross-electrophile couplings / 1, 2-Glycosyl orthoesters / C—C coupling / Stereochemistry

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Xin Wang, Anrong Chen, Shiyin Zhao, Qiang Tao, Bo Yang, Xing Zhang, Feng Zhu. Stereoselective Synthesis of C-Vinyl Glycosides via Nickel-Catalyzed Cross-Electrophile Couplings of 1, 2-Glycosyl Orthoesters and Vinyl Halides. Chinese Journal of Chemistry, 2024, 42(23): 3029-3034 DOI:10.1002/cjoc.202400651