RESUMO
o-Phthalaldehyde in combination with chiral thiols is described as a chiral reagent for the resolution of the enantiomers of alpha-H-alpha-aminonitriles and alpha-alkyl-alpha-aminonitriles. Separation of the resulting diastereomers was carried out by reversed-phase chromatography and the derivatives were detected at UV 340 nm. The identity of the diastereomeric derivatives was confirmed by LC-MS. Among the chiral thiols tested, N-acetyl-D-penicillamine and beta-mercaptoisobutyric acid gave the best resolution for the alpha-aminonitriles studied. For quantitative enantiomeric excess determination, beta-mercaptoisobutyric acid was chosen as this thiol could be obtained in high enantiomeric purity from a commercial source. The rate of the reaction of various alpha-aminonitriles with o-phthalaldehyde and beta-mercaptoisobutyric acid was studied. The accuracy of the method was investigated by a comparison of theoretical and measured enantiomeric excess.
