Regular Article
Enantioseparation of racemic 4-aryl-3,4-dihydro-2(1H)-pyrimidones on chiral stationary phases based on 3,5-dimethylanilides of N-(4-alkylamino-3,5-dinitro)benzoyl L-α-amino acids
Darko Kontrec, Vladimir Vinković, Vitomir Šunjić,
Birgit Schuiki,
Walter M.F. Fabian,
C. Oliver Kappe,
Corresponding Author
Vitomir Šunjić
Ruđer Bošković Institute, Zagreb, Croatia
Laboratory for Stereoselective Catalysis and Biocatalysis, Ruđer Bošković Institute, Bijeniçka 54, HR-10002 Zagreb, CroatiaSearch for more papers by this authorBirgit Schuiki
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorWalter M.F. Fabian
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorC. Oliver Kappe
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorDarko Kontrec, Vladimir Vinković, Vitomir Šunjić,
Birgit Schuiki,
Walter M.F. Fabian,
C. Oliver Kappe,
Corresponding Author
Vitomir Šunjić
Ruđer Bošković Institute, Zagreb, Croatia
Laboratory for Stereoselective Catalysis and Biocatalysis, Ruđer Bošković Institute, Bijeniçka 54, HR-10002 Zagreb, CroatiaSearch for more papers by this authorBirgit Schuiki
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorWalter M.F. Fabian
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorC. Oliver Kappe
Institute of Chemistry, Karl-Franzens-University Graz, Graz, Austria
Search for more papers by this authorAbstract
Three novel chiral packing materials for high-performance liquid chromatography were prepared by covalently binding of (2S)-N-(3,5-dimethylphenyl)-2-[(4-chloro-3,5-dinitrophenyl)carbonylamino]propan-amide (7), (2S)-N-(3,5-dimethylphenyl)-2-[(4-chloro-3,5-dinitrophenyl)carbonylamino]-4-methylpentanamide (8), and (2S)-N-(3,5-dimethylphenyl)-2-[(4-chloro-3,5-dinitrophenyl)carbonyl-amino]-2-phenylacetamide (9) to aminopropyl silica. The resulting chiral stationary phases (CSPs 1–3) proved effective for the resolution of racemic 4-aryl-3,4-dihydro-2(1H)-pyrimidone derivatives (TR 1–14). The mechanism of their enantioselection, supported by the elution order of (S)-TR 13 and (R)-TR 13 and molecular modeling of the complex of the slower running (S)-TR 13 with CSP 1 is discussed. Chirality 15:550–557, 2003. © 2003 Wiley-Liss, Inc.
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