Sequential alkoxy radical fragmentation–intermolecular allylation in carbohydrate systems

The C-radical originated by β-fragmentation of carbohydrate anomeric alkoxy radicals, generated under reductive conditions by treatment of N-phthalimido glycosides with allyltri-n-butyltin/AIBN, may subsequently undergo an intermolecular allylation to give hept-1-enitol derivatives. These compounds can be useful chiral synthons for the synthesis of polyhydroxylated compounds.