Synthesis of Aminoalcohol and Oxazolidone Chiral Stationary Phases for High-Performance Liquid Chromatography

  • W. C. Ferraz Lourenço
  • D. R. Taylor
Part of the Chromatographic Society Symposium Series book series (CSSS)

Summary

Several examples of a new family of chiral stationary phases (CSPs) have been prepared by treatment of silica gel with asymmetric optically active organosilanes derived from the reactions between epoxides and amines. When a racemic epoxide reacts regiospecifically with an optically active amine, two readily separated optically active diastereoisomers are produced. We have devised procedures for attaching the resultant aminoalcohols to silica gel, along lines used previously by ourselves and others for synthesis of CSPs via organosilane precursors. Protection of the reactive aminoalcohol function was essential to avoid polymerisation prior to bonding.

Keywords

Hydrolysis Chloroform Toluene Adduct Hydrochloride 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    W. H. Pirkle and J. M. Finn, J. Chromatogr, 192: 143–158 (1980).CrossRefGoogle Scholar
  2. 2.
    W. H. Pirkle, M. H. Hyun and B. Bank, J. Chromatogr, 316: 585–604 (1984).CrossRefGoogle Scholar
  3. 3.
    W. H. Pirkle and J. E. McCune, J. Chromatogr, 441: 311–322 (1988).CrossRefGoogle Scholar
  4. 4.
    Y. Dobashi and S. Hara, J. Org. Chem, 52: 2490–2496 (1987).CrossRefGoogle Scholar
  5. 5.
    J. B. Hyne, J. Am. Chem. Soc, 81: 6058–6061 (1959).CrossRefGoogle Scholar
  6. 6.
    L. Teng and R B. Bruce, J. Labelled Compd. Radiopharm, 15: 321–328 (1978).CrossRefGoogle Scholar
  7. 7.
    D. R. Taylor, “International Symposium on Chiral Separations”, Guildford, UK, unpublished results (1987).Google Scholar
  8. 8.
    G. J. Bridger, PhD Thesis, UMIST (1987).Google Scholar
  9. 9.
    W. H. Pirkle, M. Hyun, A. Tsipouras, B. C. Hamper and B. Banks, J. Pharm. Biomed. Anal., 2: 173–181 (1984).PubMedCrossRefGoogle Scholar
  10. 10.
    C. Rosini, C. Bertucci, D. Pini, P. Altemura and P. Salvadori, Tetrahedron Lett., 26: 3361–3364 (1985).CrossRefGoogle Scholar
  11. 11.
    I. Shibata, A. Baba, H. Iwasaki and H. Matsuda, J. Org. Chem, 51: 2177–2184 (1986).CrossRefGoogle Scholar
  12. 12.
    B. M. Trost and A. R. Sudhaker, J. Am. Chem. Soc, 109: 3792–3794 (1987).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1991

Authors and Affiliations

  • W. C. Ferraz Lourenço
    • 1
  • D. R. Taylor
    • 1
  1. 1.Chemistry DepartmentUMISTManchesterUK

Personalised recommendations