CHROMATOGRAPHIC RESOLUTION OF RACEMIC ALPHA-HALOCARBOXYLIC ACIDS AND O-SUBSTITUTED ALPHA-HYDROXYCARBOXYLIC ACIDS VIA DIASTEREOMERIC N-ACYLOXAZOLIDINONES

Abstract

Diastereomeric pairs of N-acyloxazolidinones, derived from (4R,5S)-4-methyl-5-phenyl-2-oxazolidinon (as a chiral derivatizing agent) and racemic alpha-halocarboxylic acids or O-substituted alpha-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.