Summary
The enantiomeric resolution of seven racemic sulphoxides on chiral stationary phases has been investigated by gas and liquid chromatography. In gas chromatography the separations were performed on octakis-(2,6-di-O-pentyl-3-O-butyryl)-γ-cyclodextrin (FS Lipodex-E) and heptakis-(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin (DMP-β-CD). Both stationary phases were suitable for separation of the enantiomers of the sulphoxides. With one exception for each series all racemetes could be resolved on both stationary phases; FS Lipodex-E was more enantioselective than DMP-β-CD, whereas the latter seemed more generally applicable. Liquid chromatographic separations with Chiralcel-OB as stationary phase were significantly improved by optimization of mobile phase composition and temperature. Resolution factors up to Rs=6 were achieved indicating that the improved separations could now be easily used for preparative purposes.
References
P.W.B. Harrison, J. Kenyon, H. Phillips, J. Chem. Soc. (1926) 2079.
K. K. Andersen, in “The Chemistry of Sulphones and Sulphoxides” S. Patai, R. Rappoport, C. J. M. Stirling (eds), Wiley, Chichester, 1988, pp. 55–94.
P. Newman, “Optical Resolution Procedures for Chemical Compounds,” Vol. 4, Parts I and II, Optical Resolution Information Center, Manhattan College, Riverdale, NY, 1993.
A. J. Walker, Tetrahedron: Asymmetry,3, 961 (1992).
C. Hansch, P. G. Sammes, J. B. Taylor (eds), Comprehensive Medical Chemistry, Pergamon Press, Oxford, Vol. 6, 1990, 242.
G. Farina, F. Montanari, A. Negrini, Gazz. Chim. Ital.89, 1548 (1959).
W. H. Pirkle, D. W. House, J. Org. Chem.,44, 1957 (1979).
W. H. Pirkle, J. M. Finn, J. L. Schreiner, B. C. Hamper J. Am. Chem. Soc.,103, 3964 (1981).
W. H. Pirkle, D. W. House, J. M. Finn, J. Chromatogr.252, 297 (1982).
S. Allenmark, L. Nielsen, W. H. Pirkle, Acta Chem. Scand.37, 325 (1983).
G. Gargaro, F. Gasparrini, D. Misiti, G. Palmieri, M. Pierine, C. Villani Chromatographia,24, 505 (1987).
S. Allenmark, B. Bomgren J. Chromatogr.252, 297 (1982).
S. Allenmark, B. Bomgren, H. Borén, P.-O. Lagerström, Anal. Biochem.136, 293 (1984).
K. Balmér, B.-A. Persson, P.-O. Lagerström, J. Chromatogr. A660, 269 (1994).
A. Ichida, T. Shibata, I. Okamoto, Y. Yuki, H. Namikoshi, Y. Toga, Chromatographia19, 280 (1984).
I. Wainer, M. C. Alembik, C. R. Johnson, J. Chromatogr.361, 374 (1986).
M. H. Gaffney, R. M. Stiffin, I. W. Wainer, Chromatographia27, 15 (1989).
E. Küsters, V. Loux, E. Schmid, Ph. Floersheim, J. Chromatogr. A666, 421 (1994).
S. A. Matlin, M. E. Tiritan, Q. B. Cass, D. R. Boyd, Chirality8, 147 (1996).
E. Bayer, Z. Naturforsch.38B, 1281 (1983).
E. Bayer, E. Küsters, G. J. Nicholson, H. Frank J. Chromatogr.320, 393 (1985).
W. A. König, Gas Chromatographic Enantiomer Separation with Modified Cyclodextrins, Hüthig., 1992, pp. 103–104.
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Küsters, E., Gerber, G. Enantiomeric separation of racemic sulphoxides on chiral stationary phases by gas and liquid chromatography. Chromatographia 44, 91–96 (1997). https://doi.org/10.1007/BF02466521
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DOI: https://doi.org/10.1007/BF02466521