Synthesis of stereoisomeric alkyl- and phenyl-substituted 5-cyanopiperidine-3,4-diols
Abstractα-Hydroxy-Β-[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.