Enantioseparation of carbonyl compounds by high-performance liquid chromatography based on diastereomer formation

Abstract

The optically active fluorescent tagging reagents, 4-(2-carbazoylpyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole [R(+)-and S(–)-NBD-ProCZ] and 4-(2-carbazoylpyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole [R(+)-and S(–)-DBD-ProCZ], react with enantiomers of aldehydes and ketones under mild conditions (65 °C for 10 min) in the presence of trichloroacetic acid (TCA). Fluorescent hydrazone diastereomers derived from some chiral ketones were separated by reversed-phase and/or normal-phase high-performance liquid chromatography, on achiral columns.