Note on the use of reciprocity of chiral recognition in designing liquid chromatographic chiral stationary phases.

A new high-performance liquid chromatographic chiral stationary phase (CSP) was prepared from (S)-N-(3,5-dimethylbenzoyl)leucine N-phenyl N-allyl amide. The new CSP was applied for the resolution of N-(3,5-dinitrobenzoyl)-alpha-amino amides and esters and the chromatographic resolution results were compared with those on another CSP derived from (S)-N-(3,5-dimethoxylbenzoyl)leucine N-phenyl N-allyl amide. The new CSP was found to exert greater enantioselectivity than the other one. These results are contrary to what was expected from the reciprocity of chiral recognition. From these results it was concluded that the reciprocity of chiral recognition should be used with some degree of care in developing effective CSPs or in predicting chromatographic resolution behaviors.