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Synfacts 2008(12): 1325-1325  
DOI: 10.1055/s-0028-1083590
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Saturated C-Glycosides via Ni-Catalyzed Diastereoselective Cross-Coupling

Contributor(s): Paul Knochel, Andreas J. Wagner
H. Gong, M. R. Gagné*
University of North Carolina at Chapel Hill, USA
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

A Ni-catalyzed Negishi cross-coupling leading to C-glycosides is described. NiCl2/PyBox in dimethylimidazolidinone (DMI) efficiently enables the synthesis of C-alkyl glycosides whereas for arylation the combination of Ni(cod)2/tert-Bu-terpy in DMF is more effective. While the reaction proceeds in moderate yields and β-selectivity for glucose derivatives, it is high-yielding and β-selective for mannosides.