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Chemistry of Heterocyclic Compounds

, Volume 21, Issue 12, pp 1355–1362 | Cite as

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

  • G. V. Grishina
  • V. M. Potapov
  • S. A. Abdulganeeva
  • E. Yu. Korchagina
Article

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.

Keywords

Methyl Organic Chemistry Optical Property Absolution Configuration Asymmetric Synthesis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • G. V. Grishina
    • 1
  • V. M. Potapov
    • 1
  • S. A. Abdulganeeva
    • 1
  • E. Yu. Korchagina
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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