The selectivity of metallation in 3- and 3,4-substituted 5-methylisoxazoles by n-butyl-lithium is determined by the influence of exo- and endo-cyclic heteroatoms. In contrast, both series of isoxazoles are metallated specifically at the C-5 methyl group by lithium di-isopropylamide.
J. Gainer, G. A. Howarth, W. Hoyle, S. M. Roberts and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1976, 994 DOI: 10.1039/P19760000994
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