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

作　　者：Xin Wang Anrong Chen Shiyin Zhao Qiang Tao Bo Yang Xing Zhang Feng Zhu 

机构地区：[1]Pingyuan Laboratory,Xinxiang,Henan 453007,China [2]Schol 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

出　　处：《Chinese Journal of Chemistry》2024年第23期3029-3034,共6页中国化学(英文版)

基　　金：sponsored by the National Key R&D Program of China(Grant No.2023YFA1508800);National Natural Science Foundation of China(Grant No.22301178);Shanghai Pilot Program for Basic Research-Shanghai Jiao Tong University(Grant No.21TQ1400210);Fundamental Research Funds for the Central Universities(Grant No.22x010201631);the Open Grant from the Pingyuan Laboratory(2023PY-OP-0102);Excellent Young Scientists Fund Program(Overseas);Natural Science Foundation of Shanghai(Grant No.21ZR1435600).

摘　　要：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.

关 键 词：Glycosylation Nickel catalysis Cross-electrophile couplings 1 2-Glycosyl orthoesters C-C coupling STEREOCHEMISTRY 

分 类 号：O62[理学—有机化学]