Intramolecular Nitrile Oxide—Alkene Cycloaddition of Sugar Derivatives with Unmasked Hydroxyl Group(s).

Intramolecular nitrile oxide−alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.