Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A New Chiral Stationary Phase Derived from Cyclohexylamide Derivative of (S)-Naproxen for the Liquid Chromatographic Resolution of Enantiomers

  • Published : 1995.10.20
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Abstract

A new chiral stationary phase (CSP 2) derived from cyclohexylamide of (S)-naproxen has been prepared. CSP 2 has shown greater enantioselectivities for the two enantiomers of N-(3,5-dinitrobenzoyl)-a-amino esters and amides than the CSP derived from 3,5-dimethylanilide of (S)-naproxen (CSP 1) as expected from the reciprocity conception of chiral recognition. However, CSP 2 has been found to be worse than CSP 1 in resolving N-(3,5-dinitrobenzoyl)-a-arylalkylamines, supporting the previously proposed chiral recognition mechanism which utilizes the 3,5-dimethylphenyl group of CSP 1 as an alternative π-basic interaction site. In addition, CSP 2 has been found to be reasonably good in resolving the two enantiomers of a variety of other π-acidic racemates.

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References

  1. Chem. Rev. v.89 Pirkle, W. H.;Pochapsky, T. C.
  2. J. chromatogr. Sci. v.30 Taylor, D. R.;Maher, K. J.
  3. J. Org. Chem. v.49 Pirkle, W. H.;Hyun, M. H.
  4. J. Chromatogr. v.393 Hyun, M. H.;Pirkle, W. H.
  5. J. Liq. Chromatogr. v.13 Hyun, M. H.;Kim, M. H.
  6. Chem. Lett. Hyun, M. H.;Min, C.-S.
  7. Chirotechnology : Industrial Synthesis of Optically Active Compounds Sheldon, R. A.
  8. US Pat. v.4 Doyle, T. D.;Brunner, C. A.;Smith, E.
  9. J. Chromatogr. v.589 Oliveros, L.;Mingullon, C.;Desmazieres, B.;Desbene, P.-L.
  10. J. Org. Chem. v.57 Pirkle, W. H.;Welch, C. J.;Lamm, B.
  11. J. Chromatogr. A v.659 Pirkle, W. H.;Spence, P. L.;Lamm, B.;Welch, C. J.
  12. Chem. Lett. Hyun, M. H.;Hwang, S.-Y.;Ryoo, J.-J.
  13. Bull. Kor. Chem. Soc. v.15 Hyun, M. N.;Jin, J. S.;Ryoo, J.-J.;Jyung, K. K.
  14. Bull. Kor. Chem. Soc. v.16 Hyun, M. H.;Jin, J. S.;Na, M. S.;Jyung, K. K.
  15. J. Chromatogr. A v.696 Hyun. M. H.;Cho, Y. J.;Ryoo, J.-J;Jyung, K. K.;Heo, G. S.
  16. Bull. Kor. Chem. Soc. v.16 Hyun, M. H.;Cho, Y. J.;Min, C. S.;Ryoo, J.-J.
  17. J. Org. Chem. v.46 Pirkle, W. H.;Finn, J. M.
  18. J. Liq. Chromatogr. v.14 Pirkle, W. H.;Welch, C. J.
  19. Bull. Kor. Chem. Soc. v.10 Hyun, M. H.;Min, C.-S.
  20. Bull. Kor. Chem. Soc. v.12 Hyun, M. H.;Kim, M.-S.