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Steric control of the asymmetric synthesis of N-substitued 2-methyl-4-piperidones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Transmission of the iodomethylate of 1,2-dimethyl-4-piperidone by (S)-sec-butylamine gives 1-(S-sec-butyl)-2S-methyl-4-piperidone in 33% optical yield while transamination by (S)-l-methyl-2-phenylethylamine gives a 1:1 diastereomeric mixture of 1-(l-methyl-2-phenylethyl)-2 -methyl-4-piperidone.The decrease in the optical yield is related to the facile opening of the piperidone ring at the C-N bond with subsequent recyclization. The13C MIR data indicate that all the diastereomers of the 4-piperidones obtained are in the chair conformation with predominantly equatorial orientation of the methyl group at C(2). The chiral optical properties were studied and the absolution configurations of the 4-piperidones obtained were established.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva & E. Yu. Korchagina

Authors
  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. E. Yu. Korchagina
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1648–1655, December, 1985.

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Grishina, G.V., Potapov, V.M., Abdulganeeva, S.A. et al. Steric control of the asymmetric synthesis of N-substitued 2-methyl-4-piperidones. Chem Heterocycl Compd 21, 1355–1362 (1985). https://doi.org/10.1007/BF00842959

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  • DOI: https://doi.org/10.1007/BF00842959

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