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

Author:

Wang Xin123,Chen Anrong3,Zhao Shiyin3,Tao Qiang23,Yang Bo3,Zhang Xing2,Zhu Feng13

Affiliation:

1. Pingyuan Laboratory Xinxiang Henan 453007 China

2. School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu 210023 China

3. China Frontiers Science Center for Transformative Molecules (FSCTM), Center for Chemical Glycobiology, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study Shanghai Jiao Tong University Shanghai 200240 China

Abstract

Comprehensive SummaryA 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.

Funder

Natural Science Foundation of Shanghai Municipality

Fundamental Research Funds for the Central Universities

National Science Foundation of Sri Lanka

National Key Research and Development Program of China

Publisher

Wiley

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