Oxidative cycloaddition of aldoximes with unsaturated substrates provides an efficient approach to the formation of heterocyclic products such as isoxazolines, isoxazoles, oxadiazoles, or dioxazoles. Various heterocyclic products can be prepared by the oxidative cyclization of aldoximes using hypervalent iodine(III) reagents. For example, isoxazolines can be easily prepared from aldoximes and alkenes in the presence of hypervalent iodine oxidants. However, a synthetic approach to isoxazoline-fused bicyclic compounds mediated by iodine(III) species was not previously reported. Herein, we report an efficient synthetic procedure for preparation of isoxazoline-fused bicyclic heterocycles from various aldoximes and 1-propene-1,3-sultone or cyclic phospholene oxide using hypervalent iodine(III) reagent. The oxidative cycloaddition of aldoximes with heterocyclic alkenes using Koser’s reagent proceeds at room temperature to give the corresponding bicyclic heterocycles in low to good yields.

Oxidative heterocyclization of aldoximes with heterocyclic alkenes mediated by hypervalent iodine reagent

255th National Meeting (2018)

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