Synthesis of stereoisomeric alkyl- and phenyl-substituted 5-cyanopiperidine-3,4-diols

-Hydroxy--[N-(2-cyanoethyl)amino]ketones were obtained by the reaction of methyl- and phenyl-substituted 2-acyloxiranes with 3-alkylaminopropionitriles. Treatment of the products with sodium tert-butoxide gave stereoisomeric 5e-cyanopiperidine-3,4-diols, the three-dimensional structures of which were established by means of spectral data, as well as by means of isomerization and oxidation with periodic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1207–1211, September, 1986.