Intramolecular 1,5-hydrogen atom transfer reaction promoted by phosphoramidyl and carbamoyl radicals: synthesis of 2-amino-C-glycosides

The preparation of 2-amino-C-glycosides of the hexahydro-2H-furo[3,2-b]pyrrole and octahydropyrano[3,2-b]pyrrole systems is described. A tandem 1,5-hydrogen atom transfer-radical oxidation-nucleophilic cyclisation mechanism is proposed for the intramolecular hydrogen atom transfer reaction promoted by carbamoyl and phosphoramidyl radicals employing hipervalent iodine oxidants.