Regiocontrol of Nitrile Oxide Cycloadditions to Allyl Alcohols. Synthesis of 4-Substituted and 4,4-Disubstituted 5-Hydroxymethyl-2-isoxazolines

Article abstract of DOI:10.1016/S0040-4039(00)91622-8

The first regiocontrol of nitrile oxide cycloadditions is described.Reaction of benzonitrile oxide with (E)-2-butenol is highly accelerated by the presence of a magnesium alkoxide, and this reaction proceeds in an exclusively regioselective manner to produce 5-hydroxymethyl-4-methyl-3-phenyl-2-isoxazoline as the sole cycloadduct.Synthetic applications to other substituted allyl alcohols are discussed.