Enantioselective separation of enantiomeric amides on three amylose‐based chiral stationary phases: Effects of backbone and carbamate side chain chiralities

Abstract

A series of enantiomeric amides have been chromatographed on three amylose-based chiral stationary phases (CSPs): amylose tris(3,5-dimethylphenylcarbamate) (AD-CSP), amylose tris (S-phenylethylcarbamate) (AS-CSP), and amylose tris(R-phenylethyl-carbamate) (AR-CSP). The relative retentions and enantioselectives of the solutes on the three CSPs were compared and basic structure-retention relationships developed to describe the chromatographic results. The data indicate that for these solutes the observed elution order was a function of the chirality of the amylose backbone, while the magnitude of the enantioselective separations was affected by the chirality of the carbamate side chain. Chirality 9:173–177, 1997. © 1997 Wiley-Liss, Inc.