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A library of 36 L-amino acid anilides, which are potential selectors for chiral HPLC, was synthesized in solution and attached to functionalized macroporous polymer beads. The best selector from the library was identified by a deconvolution process using the HPLC separation of several racemic N-(3,5-dinitrobenzoyl)-[Alpha]-amino acid alkylamides as a probe. In each deconvolution step, a series of chiral stationary phases (CSPs) containing a subset of the amino acid anilide selector library was screened for enantioselectivity. After the best CSP was chosen, the library was further deconvoluted until the single best selector was found. The highest selectivity was obtained with a L-proline-1-indananilide that exhibited [Alpha] values up to 23 under normal-phase HPLC conditions. In addition, six CSPs were prepared using individual selectors from the library, and screening results indicate that the deconvolution process indeed led to the most selective receptor.

Porous size monodisperse methacrylate beads containing amino and hydroxyl groups, which can be used as a platform for the production of chiral separation media, have been prepared using the staged templated suspension polymerization process. The monomers 2-hydroxyethyl methacrylate and several tert-butoxycarbonyl-protected aminoalkyl methacrylates were used for the preparation of both hydroxyl- and amino-functionalized beads. Attachment of a chiral selector based on L-valine-3,5-dimethylanilide through a carbamate and a urea linkage, respectively, provides chiral stationary phases with excellent enantioselectivities in the separation of the enantiomers of 3,5-dinitrobenzamido derivatives of [Alpha]-amino acids. For comparison purposes, a separation medium was also prepared by the direct polymerization of a chiral monomer analogous to the hydroxyethyl methacrylate-based stationary phase. The chiral stationary phases prepared with the N-methyl-2-aminoethyl methacrylate platform exhibit the best selectivity, and separation factors as high as 15 were achieved under normal-phase HPLC conditions.