Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide–alkene cycloaddition on d-ribose derived nitriles: an efficient synthetic route to isoxazoline fused five and six membered carbocycles

• MK-10/chloramine T oxidation and intramolecular nitrile oxide–alkene cycloaddition.
• INOC of d-ribose derived nitriles with one or more free hydroxyl groups.
• Isoxazoline fused five and six membered carbocycles were synthesized stereoselectively.

An efficient synthetic route to isoxazoline fused carbocycles from carbohydrate scaffolds that comprise of free hydroxyl group(s) is described with high regio- and stereoselectivity. Montmorillonite K-10/chloramine T oxidation and in situ intramolecular nitrile oxide–alkene cycloaddition (INOC) of d-ribose derived oximes have been developed for the diversity oriented synthesis of isoxazoline fused five and six membered carbocycles.

Figure optionsDownload as PowerPoint slide