Visible light photoredox catalysis is increasingly finding applications in the asymmetric synthesis of complex organic molecules.  Synthetic methods based on visible light catalysis benefit from orthogonal functional group compatibility, typically mild redox conditions, and reaction control mediated by the presence or absence of a visible light source.  Visible light photoredox catalysis has been adapted to the activation and coupling of thioglycoside donors, resulting in formation of O-glycosidic linkages.  Results of these experiments, as well as investigations into the coupling mechanism, which is proposed to occur via an oxacarbenium ion intermediate, will be presented.  Further application to the preparation of complex oligosaccharides and glycosylated natural products will also be presented.

Photocatalytic <i>O</i>-glycosylation of thioglycosides mediated by visible light

244th National Meeting (2012)

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Photocatalytic O-glycosylation of thioglycosides mediated by visible light