Biselector enantioselective stationary phases for HPLC: dependence of the chiral discrimination properties on stereochemistry and chemical nature of each unit of the chiral auxiliary

Optically active 1-(1-naphthyl)ethylamine, N-3,5-dinitrobenzoylphenylglycine and N-3,5-dinitrobenzoylleucine were used as chiral building blocks to prepare three new enantiomerically pure bifunctional chiral auxiliaries for enantioselective HPLC, belonging to a family of biselector systems, the first example of which (CSP1) has been described previously. These compounds were covalently linked to silica gel to produce three chiral stationary phases (CSPs 2-4), whose enantiodiscriminating capability towards the HPLC resolution of selected racemic compounds was assessed. The obtained results allowed us to establish the influence of the stereochemistry and/or the chemical structure of each chiral moiety of the biselector system on their enantiorecognition properties. (C) 2002 Elsevier Science Ltd. All rights reserved.