Aza-Ferrier rearrangement of glycals with amides promoted by molecular iodine

Amidoglycosidation of tri-O-acetyl-d-glucal with different N-nucleophiles such as t-butyl carbamate, N-benzyl carbamate, N-ethyl carbamate, tosyl amide, and mesyl amide has been achieved using an equimolar amount of molecular iodine under mild and neutral conditions to afford the corresponding N-glycosyl amides in good yields with a preferential α-anomeric selectivity. The use of iodine makes this method simple, convenient, and cost-effective. This is the first report on aza-Ferrier rearrangement using molecular iodine.