A Combinatorial Approach to Recognition of Chirality: Preparation of Highly Enantioselective Aryl-Dihydropyrimidine Selectors for Chiral HPLC
| Autor: | Jean M. J. Fréchet, Kevin M. Lewandowski, Peter Murer, Frantisek Svec |
|---|---|
| Rok vydání: | 1998 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Stereochemistry Aryl Enantioselective synthesis Substituent Stereoisomerism General Chemistry Combinatorial chemistry Chiral column chromatography chemistry.chemical_compound Pyrimidines chemistry Combinatorial Chemistry Techniques Enantiomer Chirality (chemistry) Lead compound Chromatography High Pressure Liquid Alkyl |
| Zdroj: | Scopus-Elsevier |
| ISSN: | 1520-4774 1520-4766 |
| DOI: | 10.1021/cc980014p |
| Popis: | A parallel library of 108 4-aryl-1,4-dihydropyrimidine (DHPM) enantiomers, which are potential selectors for chiral HPLC separations, was synthesized using the single-step Biginelli multicomponent condensation. The individual compounds were screened by observing the enantioselectivity for resolution on a "brush-type" L-(3,5-dinitrobenzoyl)leucine-based chiral stationary phase, and separation factors alpha up to 12 were achieved. The best candidates from the library contained an ortho-substituted aromatic group at C4 carbon atom of the pyrimidine ring and an alkyl substituent at N1 nitrogen atom. Resolution of the enantiomers of the lead compound, 4-(9-phenanthryl)-DHPM 8, using semipreparative chiral HPLC followed by attachment to monodisperse macroporous aminomethacrylate beads, provided the novel polymer based chiral stationary phase with good enantioselectivities in the resolution of several pi-acidic aryl-dihydropyrimidines and derivatized profens. In addition, 3,5-dinitrobenzamido derivatives of alpha-amino acids could be resolved under normal phase HPLC conditions with separation factors up to 8. |
| Databáze: | OpenAIRE |
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