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Issue 0, 1986
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Knoevenagel reactions with β-oxo acids. Regiospecific enol equivalents for syntheses of α,β-unsaturated ketones and of some β-ketols

Abstract

3-Oxobutanoic acid reacts with aliphatic aldehydes in the presence of pyridine to give α,β-unsaturated methyl ketones in good yields. Analogous results were obtained with a series of other β-oxo acids. Synthesis of (E)-7-methyloct-4-en-3-one, a major constituent of the marine sponge Plakortis zygompha, has been carried out using this methodology. Aromatic aldehydes are generally less reactive under these conditions but give β-ketols when the phenyl ring bears an electron-withdrawing substituent. Some observations on the mechanism of the reaction between 3-oxobutanoic acid and benzaldehyde are presented.

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Article type: Paper
DOI: 10.1039/P19860002137
Citation: J. Chem. Soc., Perkin Trans. 1, 1986, 2137-2142
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    Knoevenagel reactions with β-oxo acids. Regiospecific enol equivalents for syntheses of α,β-unsaturated ketones and of some β-ketols

    D. H. Grayson and M. R. J. Tuite, J. Chem. Soc., Perkin Trans. 1, 1986, 2137
    DOI: 10.1039/P19860002137

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