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

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Book cover Recent Advances in Chiral Separations

Part of the book series: Chromatographic Society Symposium Series ((CSSS))

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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.

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References

  1. W. H. Pirkle and J. M. Finn, J. Chromatogr, 192: 143–158 (1980).

    Article  CAS  Google Scholar 

  2. W. H. Pirkle, M. H. Hyun and B. Bank, J. Chromatogr, 316: 585–604 (1984).

    Article  CAS  Google Scholar 

  3. W. H. Pirkle and J. E. McCune, J. Chromatogr, 441: 311–322 (1988).

    Article  CAS  Google Scholar 

  4. Y. Dobashi and S. Hara, J. Org. Chem, 52: 2490–2496 (1987).

    Article  CAS  Google Scholar 

  5. J. B. Hyne, J. Am. Chem. Soc, 81: 6058–6061 (1959).

    Article  CAS  Google Scholar 

  6. L. Teng and R B. Bruce, J. Labelled Compd. Radiopharm, 15: 321–328 (1978).

    Article  CAS  Google Scholar 

  7. D. R. Taylor, “International Symposium on Chiral Separations”, Guildford, UK, unpublished results (1987).

    Google Scholar 

  8. G. J. Bridger, PhD Thesis, UMIST (1987).

    Google Scholar 

  9. W. H. Pirkle, M. Hyun, A. Tsipouras, B. C. Hamper and B. Banks, J. Pharm. Biomed. Anal., 2: 173–181 (1984).

    Article  CAS  PubMed  Google Scholar 

  10. C. Rosini, C. Bertucci, D. Pini, P. Altemura and P. Salvadori, Tetrahedron Lett., 26: 3361–3364 (1985).

    Article  CAS  Google Scholar 

  11. I. Shibata, A. Baba, H. Iwasaki and H. Matsuda, J. Org. Chem, 51: 2177–2184 (1986).

    Article  CAS  Google Scholar 

  12. B. M. Trost and A. R. Sudhaker, J. Am. Chem. Soc, 109: 3792–3794 (1987).

    Article  CAS  Google Scholar 

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© 1991 Plenum Press, New York

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Lourenço, W.C.F., Taylor, D.R. (1991). Synthesis of Aminoalcohol and Oxazolidone Chiral Stationary Phases for High-Performance Liquid Chromatography. In: Stevenson, D., Wilson, I.D. (eds) Recent Advances in Chiral Separations. Chromatographic Society Symposium Series. Springer, New York, NY. https://doi.org/10.1007/978-1-4684-8282-9_11

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  • DOI: https://doi.org/10.1007/978-1-4684-8282-9_11

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4684-8284-3

  • Online ISBN: 978-1-4684-8282-9

  • eBook Packages: Springer Book Archive

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