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Optical Resolution of Racemic α-Hydroxycarboxylic Acids on a Dynamic Chiral Stationary Phase Derived from (S)-Leucinol by Ligand Exchange Chromatography

  • Hyun, Myung-Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Jung-In (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Cho, Yoon-Jae (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Ryoo, Jae-Jeong (Department of Chemical Education, Kyungpook National University)
  • Published : 2004.11.20
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References

  1. A Practical Approach to Chiral Separation by Liquid Chromatography; Subramanian, G., Ed.; VCH: Weiheim, 1994
  2. Ahuja, S. Chiral Separations by Chromatography; Oxford University Press: American Chemical Society, Washington, D.C., 2000
  3. Aboul-Enein, H. Y.; Ali, I. Chiral Separations by Liquid Chromatography and Related Technologies, Chromatographic Science Series Vol. 90; Marcel Dekker, Inc.: New York, 2003.
  4. Okamoto, Y.; Kawashima, M.; Hatada, K. J. Am. Chem. Soc. 1984, 237, 473.
  5. Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. https://doi.org/10.1080/01483918608076644
  6. Armstrong, D. W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen, J. R. Anal. Chem. 1994, 66, 1473. https://doi.org/10.1021/ac00081a019
  7. Hyun, M. H.; Cho, Y. J.; Jin, J. S. J. Sep. Sci. 2002, 25, 648. https://doi.org/10.1002/1615-9314(20020701)25:10/11<648::AID-JSSC648>3.0.CO;2-D
  8. Lee, W.; Baek, C.-S.; Lee, K. Bull. Korean Chem. Soc. 2002, 23, 1677. https://doi.org/10.5012/bkcs.2002.23.11.1677
  9. Hyun, M. H.; Min, H. J.; Cho, Y. J. Bull. Korean Chem. Soc. 2003, 24, 911. https://doi.org/10.5012/bkcs.2003.24.7.911
  10. Pirkle, W. H.; Welch, C. J.; Lamm, B. J. Org. Chem. 1992, 57, 3854. https://doi.org/10.1021/jo00040a026
  11. Hyun, M. H.; Cho, Y. J.; Baik, I.-K. Bull. Korean Chem. Soc. 2002, 23, 1291. https://doi.org/10.5012/bkcs.2002.23.9.1291
  12. Davankov, V. A. Enantiomer 2000, 5, 209.
  13. Kurganov, A. J. Chromatogr. A 2001, 906, 51. https://doi.org/10.1016/S0021-9673(00)00502-1
  14. Davankov, V. A. J. Chromatogr. A 2003, 1000, 891. https://doi.org/10.1016/S0021-9673(03)00304-2
  15. Hyun, M. H.; Lim, N.-E.; Choi, S.-N. Bull. Korean Chem. Soc. 1991, 12, 594.
  16. Hyun, M. H.; Ryoo, J.-J.; Lim, N.-E. J. Liq. Chromatogr. 1993, 16, 3249. https://doi.org/10.1080/10826079308019646
  17. Hyun, M. H.; Yang, D. H.; Kim, H. J.; Ryoo, J.-J. J. Chromatogr. A 1994, 684, 189. https://doi.org/10.1016/0021-9673(94)00595-8
  18. Hyun, M. H.; Ryoo, J.-J. J. Liq. Chromatogr. Rel. Technol. 1996, 19, 2635. https://doi.org/10.1080/10826079608014044
  19. Hyun, M. H.; Han, S. C.; Lee, C. W.; Lee, Y. K. J. Chromatogr. A 2002, 950, 55. https://doi.org/10.1016/S0021-9673(02)00035-3
  20. Hyun, M. H.; Han, S. C.; Whangbo, S. H. J. Chromatogr. A 2003, 992, 47. https://doi.org/10.1016/S0021-9673(03)00276-0
  21. Hyun, M. H.; Han, S. C. Whangbo, S. H. Biomed. Chromatogr. 2003, 17, 292. https://doi.org/10.1002/bmc.237
  22. Hyun, M. H.; Whangbo, S. H.; Cho, Y. J. J. Sep. Sci. 2003, 26, 1615. https://doi.org/10.1002/jssc.200301588
  23. Coppola, G. M.; Schuster, H. F. ${\alpha}$-Hydroxy Acids in Enantioselective Syntheses; Wiely-VCH: Weinheim, 1997.
  24. Hyun, M. H.; Min, C.-S. Bull. Korean Chem. Soc. 1989, 10, 578.
  25. Hyun, M. H.; Kang, M. H.; Han, S. C. J. Chromatogr. A 2000, 868, 31. https://doi.org/10.1016/S0021-9673(99)01140-1
  26. Gubitz, G.; Mihellyes, S. Chromatographia 1984, 19, 257. https://doi.org/10.1007/BF02687749
  27. Katoh, H.; Ishida, T.; Baba, Y.; Kiniwa, H. J. Chromatogr. A 1989, 473, 241. https://doi.org/10.1016/S0021-9673(00)91305-0
  28. Gubitz, G.; Mihellyes, S.; Kobinger, G.; Wutte, A. J. Chromatogr. A 1994, 666, 91. https://doi.org/10.1016/0021-9673(94)80372-2
  29. Chilmonczyk, Z.; Ksycinska, H.; Cybulski, J.; Rydzewski, M.; Les, A. Chirality 1998, 10, 821. https://doi.org/10.1002/(SICI)1520-636X(1998)10:9<821::AID-CHIR8>3.0.CO;2-C
  30. Davankov, V. A.; Bochkov, A. S.; Kurganov, A. A.; Roumeliotis, P.; Unger, K. K. Chromatographia 1980, 13, 677. https://doi.org/10.1007/BF02303437

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