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 π-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 π-acidic, π-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.