(S)-leucine and [(S)-1-(1-naphthyl)ethyl]amine as chiral building blocks for a bifunctional system - Synthesis of a new chiral stationary phase and evaluation of its biselector properties in the HPLC resolution of racemic compounds

Two selectors derived from [(S)-1-(1-naphthyl)ethyl]amine and (S)-leucine h ave been chemically bonded to one another and the resulting chiral auxiliar y linked covalently to silica gel, to produce a new chiral stationary phase (CSP) for the HPLC resolution of enantiomers. The CSP is able to separate the enantiomers of some selected racemic compounds: both those resolved by Oi's CSP [derived from [1-(1-naphthyl)ethyl]amine} and those enantiodiscrim inated by Pirkle's CSP [derived from N-(3,5-dinitrobenzoyl)leucine]. The re sults obtained demonstrate that the CSP possesses the properties of an effi cient biselector system.