Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl ß-C-Glycosides.

A new strategy for the synthesis of acyl ß-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl ß-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process.