Coupling Radical and Ionic Processes: An Unusual Rearrangement Affords Sugar and C-Glycoside Derivatives

Abstract

An unusual scission–rearrangement process, which couples radical and ionic reactions, was observed with galactofuranose derivatives. This one-pot procedure afforded, in good yields, highly functionalized 1,4-dioxanes, which could be considered as six-membered-ring sugar analogues. The synthesis of C-glycoside analogues is also possible with this methodology.