MECHANISTIC EVALUATION OF THE RESOLUTION OF ALPHA-AMINO-ACIDS ON DYNAMIC CHIRAL STATIONARY PHASES DERIVED FROM AMINO-ALCOHOLS BY LIGAND-EXCHANGE CHROMATOGRAPHY

Two dynamic chiral stationary phases (CSP 7 and 12) were prepared starting from (R)-2-amino-1-propanol and (R)-alpha-phenylethylamine. The resolution of racemic alpha-amino acids on the two dynamic CSPs thus prepared were compared with previously reported resolution data on a dynamic CSP (2) derived from (1S,2R)-norephedrine. The enantioselectivity for the two enantiomers of alpha-amino acids on CSP 7 was found to be comparable to or better than that on CSP 2 while the enantioselectivity for the two enantiomers of cr-amino acids on CSP 12 was much worse than that on CSPs 2 or 7. From these results, we concluded that the phenyl functionality at the first chiral center of CSP 2 is not essential in the chiral recognition. However, the hydroxy functionality of CSPs 2 or 7 does play a very important role in the chiral recognition.