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Asymmetric synthesis and absolute configuration of 1-α-phenylethyl-2,5-dimethyl-4-piperidone isomers

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reaction of the methyl iodide of trans-1,2,5-trimethyl-4-piperidone with S-α-phenylethylamine proceeds asymmetrically and leads in 66% optical yield to the formation of the cis- and trans-diastereomeric pair of 1-(α-phenylethyl)-2,5-dimethyl-4-piperidone, in which the new asymmetric centers possess the 2S,5S- and 2S,5R-configurations, respectively. According to x-ray structural analysis, the minor trans-1-(α-phenylethyl)-2,5-dimethyl-4-piperidone component possesses the 2R,5S-configuration. The occurrence of asymmetric synthesis accompanying transamination was confirmed via the preparation of enantiomers of trans-2,5- and trans-1,2,5-trimethyl-4-piperidones.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Moscow

    G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, T. A. Gudasheva, A. A. Karapetyan, A. A. Espenbetov & Yu. T. Struchkov

  2. A. N. Nesmeyanov Institute of Organometallic Chemistry, Academy of Sciences of the USSR, Moscow

    G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, T. A. Gudasheva, A. A. Karapetyan, A. A. Espenbetov & Yu. T. Struchkov

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  1. G. V. Grishina
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  2. V. M. Potapov
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  3. S. A. Abdulganeeva
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  4. T. A. Gudasheva
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  5. A. A. Karapetyan
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  6. A. A. Espenbetov
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  7. Yu. T. Struchkov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1641–1648, December, 1986.

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Grishina, G.V., Potapov, V.M., Abdulganeeva, S.A. et al. Asymmetric synthesis and absolute configuration of 1-α-phenylethyl-2,5-dimethyl-4-piperidone isomers. Chem Heterocycl Compd 22, 1327–1333 (1986). https://doi.org/10.1007/BF00474353

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  • DOI: https://doi.org/10.1007/BF00474353

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