SYNTHESIS AND MECHANISTIC STUDY OF NOVEL PI-BASIC CHIRAL STATIONARY PHASES DERIVED FROM TYROSINE

This work was a study of novel pi-basic, chiral stationary phases (CSP s) deriving from tyrosine and bearing two stereogenic centres. These C SPs differ in the nature of the amidic substituent (n-butyl or tert-bu tyl) and by the configuration of both the chiral centres (S or R). The enantioselectivity and elution order of various 3, 5-dinitrobenzoyl d erivatives were studied using liquid and supercritical fluid chromatog raphic modes. The chromatographic data allowed determination of the in fluence of the CSP structure (also studied according to factorial desi gns) and determination of the influence of the solute structure. Chira l recognition mechanisms which are in good agreement with these observ ations are proposed. Finally, this paper reports the enantiomeric reso lution of two compounds of pharmaceutical interest (warfarin and ICI 1 76334).