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Mannich reaction in a number of six-membered heterocyclic γ,-ketones. X. Stereochemistry of the reduction and phenylation of 2, 2-dimethyl-5-dimethylaminomethyl-4-oxotetrahydropyran

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2, 2-Dimethyl-5-dimethylaminomethyl-4-oxotetrahydropyran was subjected to reduction with lithium aluminum hydride, sodium borohydride, aluminum isopropoxide, and lithium in liquid ammonia, to catalytic hydrogenation over Raney nickel, and phenylation with phenyllithium. The quantitative ratios in the resulting mixtures of stereoisomeric 2, 2-dimethyl-5-dimethylaminomethyl-4-hydroxytetrahydropyrans and their dependence on the character of the reducing agents were established by means of gas — liquid chromatography and PMR spectroscopy. The individual geometrical isomers of the amino alcohols were isolated, and their three-dimensional structures were studied by means of their PMR and IR spectra.

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Authors and Affiliations

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

    E. T. Golovin, B. M. Glukhov & L. S. Botsman

Authors
  1. E. T. Golovin
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  2. B. M. Glukhov
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  3. L. S. Botsman
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Additional information

See [1] for communication IX.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 611–616, May, 1976.

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Golovin, E.T., Glukhov, B.M. & Botsman, L.S. Mannich reaction in a number of six-membered heterocyclic γ,-ketones. X. Stereochemistry of the reduction and phenylation of 2, 2-dimethyl-5-dimethylaminomethyl-4-oxotetrahydropyran. Chem Heterocycl Compd 12, 511–516 (1976). https://doi.org/10.1007/BF00470101

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  • DOI: https://doi.org/10.1007/BF00470101

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