Synthesis and Application of New Calix[4]Arenes-Containing (R)-Phenylglycinol Chiral Stationary Phases for Enantioseparation

N-3,5-Dinitrobenzoyl-(R)-phenylglycinol silylation product was used as a high-performance liquid chromatography chiral stationary phase (CSP 1) for the resolution of various racemic samples, and some racemic samples were successfully separated. In this study, instead of the commonly used pi-acidic acyl chloride, calix[4]arenes were introduced to prepare two phenylglycinol CSPs (CSP 2, CSP 3). CSP 3 showed similar separation patterns as CSP 1 but different characteristics in specific samples. The newly prepared CSP 3 separated 10 of 13 pi-acidic, pi-basic, and oxazolidinone chiral samples and was especially useful for separating chiral oxazolidinones. In comparison between CSP 2 and CSP 3, CSP 2 separated fewer chiral samples than CSP 3 because of poor cavity and steric interactions. The newly developed C-methylcalix[4]resorcinarene derived CSP (CSP 3) will be a good model for the development of new stationary phase of this calixarene series.