November 7, 2013

Oxidative Cyclizations, the Synthesis of Aryl-Substituted C-Glycosides, and the Role of the Second Electron Transfer Step




Jake A. Smith and Kevin D. Moeller

Organic Letters (2013), 15, (22), 5818-5821.

Anodic oxidation reactions have been used to synthesize aryl- and biaryl-substituted C-glycosides. The reactions take advantage of the tendency for alcohol nucleophiles to trap nonpolar radical cations. The addition of the alcohol to the radical cation appears to be reversible, and the success of the cyclizations is dependent on the ease with which the resulting benzylic radical is oxidized.