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


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.


Methyl Organic Chemistry Optical Property Absolution Configuration Asymmetric Synthesis 
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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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