The glycosyl C–C bond confers resistance to hydrolysis and improves pharmacokinetics of related drug molecules, including nucleoside analogues. A photoredox method cross-couples glycosyl esters with a range of electrophiles to afford <i>C</i>-glycosyl analogues. The convenient preparation of the redox active glycosyl ester from native sugars and the compatibility with common furanoses exemplifies the potential of this method in medicinal chemistry. A key step is the addition of the glycosyl radical to an organonickel intermediate, which determines the diastereoselectivity.

Catalytic <i>C-</i>glycosylation and diastereoselectivity governed by the metallo-anomeric effect

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Catalytic C-glycosylation and diastereoselectivity governed by the metallo-anomeric effect