Chromatographic resolution of racemic α-halocarboxylic acids and O-substituted α-hydroxycarboxylic acids via diastereomeric N-acyloxazolidinones

Diastereomeric pairs of N-acyloxazolidinones, derived from (4R,5S)-4-methyl-5-phenyl-2-oxazolidinone (as a chiral derivatizing agent) and racemic α-halocarboxylic acids or O-substituted α-hydroxycarboxylic acids, were separated chromatographically on a large preparative scale and showed appreciable degrees of NMR-shift difference. The origins of the chromatographic separability of these diastereomers are discussed.