Synthesis of a new family of four deoxycholic acid derived chiral stationary phases and their evaluation in the HPLC resolution of racemic compounds

Four new chiral selectors obtained by suitable derivatization of the hydroxyl groups of the deoxycholic acid with two identical (homoderivatized) or different (heteroderivatized) arylisocyanates have been prepared and linked covalently to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSPs containing two identical substituents are able to enantiodiscriminate different classes of racemic compounds, or the same racemates to a different extent, a property which depends on the different electronic character of the arylcarbamate moieties. The heteroderivatized CSPs retain the character of the two homoderivatized phases: however, the relative position of the two different arylcarbamate moieties on the deoxycholic backbone strongly affects the enantiodiscrimination capability of these two CSPs.