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Updated: Aug 8, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Nickel-Catalyzed Reductive Coupling for the C-Alkyl Glycosylation of Saccharides with Alkenes
Qian Zhang1, Lai Li1, Xuqing Fang1
1Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering, Shaanxi Normal University620 West Chang'an Ave, Xi'an710119, China.
Abstract:
C-Glycosides are recognized as ideal surrogates for natural O-glycosides owing to their excellent stability against acid-catalyzed and enzymatic hydrolysis, thus holding great application potential in drug discovery and glycochemical research. Nevertheless, the stereoselective assembly of fully saturated C-alkyl glycosides remains a formidable synthetic challenge. Herein, we disclose a one-pot reductive coupling strategy between saccharides and alkenes. This protocol integrates in situ anomeric bromination with nickel-catalyzed reductive coupling, allowing the direct C-glycosylation of partially protected saccharides that bear merely a free anomeric hydroxyl group with activated alkenes represented by ethyl acrylate.
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