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Mannich reaction in six-membered heterocyclic γ-ketones

XIII. Stereochemistry of the reduction of 2,2-dimethyl-5-aminomethyl-4-oxotetrahydropyrans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The stereochemical principles of the reduction of 2,2-dimethyl-5-aminomethyl-4-oxotetrahydropyrans with lithium aluminum hydride, sodium borohydride, aluminum isopropoxide, and lithium in liquid ammonia were investigated by determination of the dependence of the quantitative ratio of the resulting epimeric amino alcohols in the mixtures on the character of the reducing agent and its concentration and the nature of the solvent. The individual geometrical isomers of the amino alcohols were isolated, and their structures were established by PMR and IR spectroscopy.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Fine Chemical Technology, 119831, Moscow

    E. T. Golovin, L. S. Pomogaeva & É. I. Strakhova

Authors
  1. E. T. Golovin
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  2. L. S. Pomogaeva
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  3. É. I. Strakhova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 318–323, March, 1978.

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Golovin, E.T., Pomogaeva, L.S. & Strakhova, É.I. Mannich reaction in six-membered heterocyclic γ-ketones. Chem Heterocycl Compd 14, 256–261 (1978). https://doi.org/10.1007/BF00470553

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  • DOI: https://doi.org/10.1007/BF00470553

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