Chemistry of Heterocyclic Compounds p. 1327 - 1333 (1986)
Update date:2022-09-26
Topics:
Grishina, G. V.
Potapov, V. M.
Abdulganeeva, S. A.
Gudasheva, T. A.
Karapetyan, A. A.
et al.
Reaction of the methyl iodide of trans-1,2-5-trimethyl-4-piperidone with S-α-phenylethylamine proceeds asymmetrically and leads in 66percent 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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