Advertisement

Enantiomeric Recognition of d- and l-Amino Acid Methyl Ester Hydrochlorides by New Chiral Bis-pyridino-18-crown-6 Substituted with Urea, and Diphenyl Groups

  • Jae-Kon Kim
  • Jaehong Kim
  • Suhee Song
  • Ok-Sang Jung
  • Hongsuk Suh
Article

Abstract

The article reports the synthesis and chiral recognition properties of a new chiral bis-pyridino-18-crown-6 (7), having urea, diphenyl, and allyloxy groups. The chiral bis-pyridino-18-crown-6 was prepared by a thirteen-steps procedure from the commercially available (S)-(+)-mandelic acid and chelidamic acid. The association constants (K a) (1.33 × 103–3.20 × 103) for enantiomeric recognition of d- and l-amino acid methyl ester hydrochlorides using the chiral bis-pyridino-18-crown-6 have been examined by 1H-NMR titration method in CDCl3 at 25 °C. The chiral bis-pyridino-18-crown-6 showed higher association constants for the d-series amino acid methyl ester (d-AlaOMe, d-LeuOMe, d-MetOMe) hydrochlorides as compared to the corresponding l-series (l-AlaOMe, l-LeuOMe, l-MetOMe) hydrochlorides.

Keywords

chiral crown ether chiral molecular recognition enantiomeric recognition host-guest hydrogen bonding 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

This work was supported by the Ministry of Information & Communications, Korea, under the Information Technology Research Center (ITRC) Support Program.

References

  1. 1.
    Grove J.T., Viski P. (1990). J. Org. Chem. 55:3628CrossRefGoogle Scholar
  2. 2.
    O’Malley S., Kodadek T. (1992). Organometallics 11:2299CrossRefGoogle Scholar
  3. 3.
    Gasparrini F., Misiti D., Borchardt A., Burger M.T., Still W.C. (1995).J. Org. Chem. 60:4314CrossRefGoogle Scholar
  4. 4.
    Helgeson R.C., Koga K., Timko J.M., Cram D.J. (1973). J. Am. Chem. Soc. 95:3021CrossRefGoogle Scholar
  5. 5.
    Chao Y., Cram D.J. (1976). J. Am. Chem. Soc. 98:1015CrossRefGoogle Scholar
  6. 6.
    Breslow R., Czarnik A.W., Lauer M., Leppkes R., Winkler J., Zimmerman S. (1986). J. Am. Chem. Soc. 108:1969CrossRefGoogle Scholar
  7. 7.
    Talma A.G., Jouin P., De Vries J.G., Troostwijk C.B., Werumeus Buning G.H., Waninge J.K., Visscher J., Kellogg R.M. (1985). J. Am. Chem. Soc. 107:3981CrossRefGoogle Scholar
  8. 8.
    Webb T.H., Suh H., Wilcox C.S. (1991). J. Am. Chem. Soc. 113:8554CrossRefGoogle Scholar
  9. 9.
    Zhang X.X., Bradshaw J.S., Izatt R.M. (1997). Chem. Rev. 97:3313CrossRefGoogle Scholar
  10. 10.
    Kyba E.P., Koga K., Siegel M.G., Sousa L.R., Cram D.J. (1973). J. Am. Chem. Soc. 95:2692 CrossRefGoogle Scholar
  11. 11.
    Pederson C.J. (1988). J. Incl. Phenom. 6:337CrossRefGoogle Scholar
  12. 12.
    Lehn J.M. (1988). J. Incl. Phenom. 6:351CrossRefGoogle Scholar
  13. 13.
    Cram D.J. (1988). J. Incl. Phenom. 6:397CrossRefGoogle Scholar
  14. 14.
    Izatt R.M., Pawlak K., Bradshaw J.S., Bruening R.L. (1991). Chem. Rev. 91:1721 CrossRefGoogle Scholar
  15. 15.
    Izatt R.M., Pawlak K., Bradshaw J.S., Bruening R.L. (1995). Chem. Rev. 95:2559 CrossRefGoogle Scholar
  16. 16.
    Suh H.S., Kim J-.K., Jung I.S., Lee S.E., Kang S.W., Park J.S. (1998). Bull. Korean Chem. Soc. 19:411Google Scholar
  17. 17.
    Kim I., Han B.H., Ha C.S., Kim J.-K., Suh H.S. (2003). Macromolecules 36:6689 CrossRefGoogle Scholar
  18. 18.
    Hirose K. (2001). J. Incl. Phenom. 39:193CrossRefGoogle Scholar
  19. 19.
    Bradshaw J.S., Huszthy P., McDaniel C.W., Zhu C.Y., Dalley N.K., Izatt R.M. (1990). J. Org. Chem. 55:3129CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Jae-Kon Kim
    • 1
  • Jaehong Kim
    • 1
  • Suhee Song
    • 1
  • Ok-Sang Jung
    • 1
  • Hongsuk Suh
    • 1
  1. 1.Department of Chemistry and Center for Plastic Information SystemPusan National UniversityGeumjeong-Gu, BusanKorea

Personalised recommendations