Stereoselective domino azidation and [3 + 2] cycloaddition: a facile route to chiral heterocyclic scaffolds from carbohydrate derived synthons

Abstract

A rapid one pot intermolecular aryl azidation and intramolecular azide-olefin cycloaddition protocol has been designed using carbohydrate precursors to generate optically active, aziridine fused oxa-aza heterocycles, related to DNA targeting anti-tumour agents which on further functionalization stereoselectively produce eight membered heterocyclic scaffolds. The structural conclusions were fully supported by a molecular modelling study based on density functional theory.