FACILE AND PREDICTABLE MEANS OF SEPARATING THE ENANTIOMERS OF 5-ARYLHYDANTOINS

The enantiomers of each member of a series of fifty-four 5-arylhydanto ins of systematically varied structure are readily separated by high-p erformance liquid chromatograpby (HPLC) on CSP 1 (commercially availab le as the Whelk-O 1) and elute in a consistent order. The separation f actors for these enantiomers of the hydantoins typically exceed two, t hus rendering preparative scale separations facile. When used with sub critical carbon dioxide containing 10% methanol, enantioselectivity is reduced but resolution, R-s, increases. A chiral recognition mechanis m accounting for these separations is presented. (C) 1997 Elsevier Sci ence B.V.