Selective functionalizations of the ring olefin bond of various commercial cyclodienes through nitrile oxide dipolar cycloaddition is described. Nitrile oxides were generated from primary nitroalkanes by Mukaiyama's method. Besides regioselectivity, the dipolar cycloadditions have been performed in view of selectivity of the ring olefin bonds. The cycloalkene-fused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.
- nitrile oxide
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