ENANTIOMERIC ENRICHMENT OF PARTIALLY RESOLVED 4-HYDROXY-2-CARBOXYMETHYLCYCLOPENTANONE DERIVATIVES BY ACHIRAL PHASE CHROMATOGRAPHY

Enantiomeric purity of the chromatographic peaks of partially resolved (R)-4-hydroxy-2-carboxymethyl-2-cyclopentenone (4), 4-hydroxy-2-metho xycarbonylmethyl-2-cyclopentenone (2), (S)-4-benzoyloxy-2-carboxymethy l-2-cyclopentenone (5), (R)-4-methoxy-2-carboxymethyl-2-cyclopentenone (6), 4-methoxy-2-methoxycarbonylmethyl-2-cyclopentenone (7) and (-)-5 -oxa-6-oxoprostaglandin E(1) C(15) epimers (1A) and (1B) in achiral no rmal-phase chromatography on silica gel is dependent on the fraction w hich is being examined. The mentioned substances exhibit an enantiomer enrichment at the beginning of the chromatographic peak and a gradual depletion in the following parts. The observed enantiomer enrichment effect can be explained by a mechanistic concept which assumes a prefe rred association between the antipodes of the solute.