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Synthesis and stereochemistry of α,β,α′,β′-diepoxy ketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Diastereomeric α,β,α′,β′-diepoxy ketones and the products of their condensation with acetone were synthesized by oxidation of cinnamoyloxiranes with alkaline hydrogen peroxide. It is shown that the acidic hydrolysis of 2-methyl-1,2,4,5-di-epoxy-3-pentanones leads to ketones of the tetrahydropyran and tetrahydrofuran series. The stereochemistry of the hydrolysis products was confirmed by chemical transformations and spectroscopy.

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Authors and Affiliations

  1. V. I. Lenin Belorussian State University, 220080, Minsk

    L. S. Stanishevskii, I. G. Tishchenko, A. M. Zvonok & N. M. Kuz'menok

Authors
  1. L. S. Stanishevskii
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  2. I. G. Tishchenko
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  3. A. M. Zvonok
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  4. N. M. Kuz'menok
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 17–21, January, 1983.

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Stanishevskii, L.S., Tishchenko, I.G., Zvonok, A.M. et al. Synthesis and stereochemistry of α,β,α′,β′-diepoxy ketones. Chem Heterocycl Compd 19, 14–18 (1983). https://doi.org/10.1007/BF00512806

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  • DOI: https://doi.org/10.1007/BF00512806

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