Regiocontrol of nitrile oxide cycloadditions to allyl alcohols. Synthesis of 4-substituted and 4,4-disubstituted 5-hydroxymethyl-2-isoxazolines

@article{Kanemasa1992RegiocontrolON,
  title={Regiocontrol of nitrile oxide cycloadditions to allyl alcohols. Synthesis of 4-substituted and 4,4-disubstituted 5-hydroxymethyl-2-isoxazolines},
  author={S. Kanemasa and M. Nishiuchi and E. Wada},
  journal={Tetrahedron Letters},
  year={1992},
  volume={33},
  pages={1357-1360}
}
Abstract 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. 
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