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Russian Journal of Organic Chemistry

, Volume 48, Issue 2, pp 214–220 | Cite as

Chiral schiff bases synthesized from terpenes of pinane series in asymmetric metall complex oxidation of sulfides

  • I. V. Il’ina
  • E. A. Koneva
  • D. V. Korchagina
  • G. E. Sal’nikov
  • A. M. Genaev
  • K. P. VolchoEmail author
  • N. F. Salakhutdinov
Article

Abstract

The absolute configuration of α-hydroxyaldehyde obtained from verbenol epoxide in the presence of clay was determined. Two new Schiff bases were synthesized from the aldehyde obtained. The compounds can be used as ligands in the asymmetric vanadium-catalyzed oxidation of sulfides to sulfoxides. The structure of initial sulfides significantly affects the value of the enantiomeric excess in the obtained sulfoxides: the highest enantiomeric excess is observed in the oxidation of thioanisole.

Keywords

Acac Enantiomeric Excess Compound VIII Verbenone Thioanisole 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Carreno, M.C., Hernandez-Torres, G., Ribagorda, M. and Urbano, A., Chem. Commun., 2009, p. 6129.Google Scholar
  2. 2.
    Pellissier, H., Tetrahedron, 2006, vol. 62, p. 5559.CrossRefGoogle Scholar
  3. 3.
    Fernandez, I. and Khiar, N. Chem. Rev., 2003, vol. 103, p. 3651.CrossRefGoogle Scholar
  4. 4.
    Hanquet, G., Colobert, F., Lanners, S., and Solladie, G., Arkivoc., 2003, vol. vii, p. 328.Google Scholar
  5. 5.
    Allin, S.M., Shuttleworth, S.J., and Page, P.C.B., Organosulfur. Chem., 1998, vol. 2, p. 97.CrossRefGoogle Scholar
  6. 6.
    Liu, K.K.-C., Sakya, S.M., O’Donnell, C.J., Flick, A.C., and Li, J., Bioorg. Med. Chem., 2011, vol. 19, p. 1136.CrossRefGoogle Scholar
  7. 7.
    Cao, J., Prisinzano, T.E., Okunola, O.M., Kopajtic, T., Shook, M., Katz, J.L., and Newman, A.H., ACS Med. Chem. Lett., 2011, vol. 2, p. 48.CrossRefGoogle Scholar
  8. 8.
    Saitoh, M., Kunitomo, J., Kimura, E., Iwashita, H., Uno, Y., Onishi, T., Uchiyama, N., Kawamoto, T., Tanaka, T., Mol, C.D., Dougan, D.R., Textor, G.P., Snell, G.P., Takizawa, M., Itoh, F., and Kori, M., J. Med. Chem., 2009, vol. 52, p. 6270.CrossRefGoogle Scholar
  9. 9.
    Khomenko, T.M., Volcho, K.P., Komarova, N.I., and Salakhutdinov, N.F., Russ. J. Org. Chem., 2008, vol. 44, p. 124.CrossRefGoogle Scholar
  10. 10.
    Andersson, T., Rohss, K., Hassan-Alin, M., and Bredberg, E., Gastroenterology., 2000, vol. 118, A1210.CrossRefGoogle Scholar
  11. 11.
    Wojaczynska, E. and Wojaczynski, J., Chem. Rev., 2010, vol. 110, p. 4303.CrossRefGoogle Scholar
  12. 12.
    Volcho, K.P. and Salakhutdinov, N.F., Usp. Khim., 2009, vol. 78, p. 494.Google Scholar
  13. 13.
    Legros, J., Dehli, J.R., and Bolm, C., Adv. Synth. Catal., 2005, vol. 347, p. 19.CrossRefGoogle Scholar
  14. 14.
    Volcho, K.P., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. J. Org. Chem., 2003, vol. 39, p. 1537.CrossRefGoogle Scholar
  15. 15.
    Khomenko, T.M., Salomatina, O.V., Kurbakova, S.Yu., Il’ina, I.V., Volcho, K.P., Komarova, N.I., Korchagina, D.V., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. J. Org. Chem., 2006, vol. 42, p. p. 1653.CrossRefGoogle Scholar
  16. 16.
    Koneva, E.A., Volcho, K.P., Korchagina, D.V., Komarova, N.I., Kochnev, A.I., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. Chem. Bull., 2008, p. 108.Google Scholar
  17. 17.
    Koneva, E.A., Khomenko, T.M., Kurbakova, S.Yu., Komarova, N.I., Korchagina, D.V., Volcho, K.P., Salakhutdinov, N.F., Tolstikov, A.G., and Tolstikov, G.A., Russ. Chem. Bull., 2008, p. 1680.Google Scholar
  18. 18.
    Koneva, E.A., Volcho, K.P., Korchagina, D.V., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. J. Org. Chem., 2009, vol. 45, p. 815.CrossRefGoogle Scholar
  19. 19.
    Kuchin, A.V., Ashikhmina, E.V., Rubtsova, S.A., and Dvornikova, I.A., Khimiya rastitel’nogo syr’ya (Chemistry of Plant Raw Material), 2009, p. 59.Google Scholar
  20. 20.
    Ashikhmina, E.V., Rubtsova, S.A., Dvornikova, I.A., and Kuchin, A.V., Russ. J. Org. Chem., 2009, vol. 45, p. 1509.CrossRefGoogle Scholar
  21. 21.
    Koneva, E.A., Korchagina, D.V., Gatilov, Yu.V., Genaev, A.M., Krysin, A.P., Volcho, K.P., Tolstikov, A.G., and Salakhutdinov, N.F., Russ. J. Org. Chem., 2010, vol. 46, p. 1109.CrossRefGoogle Scholar
  22. 22.
    Koneva, E.A., Korchagina, D.V., Genaev, A.M., Volcho, K.P., and Salakhutdinov, N.F., Russ. J. Org. Chem., 2012, vol. 48, p. 32.CrossRefGoogle Scholar
  23. 23.
    Ardashov, O.V., Il’ina, I.V., Korchagina, D.V., Volcho, K.P., and Salakhutdinov, N.F., Mendeleev Commun., 2007, vol. 17, p. 303.CrossRefGoogle Scholar
  24. 24.
    Il’ina, I.V., Kurbakova, S.Yu., Volcho, K.P., and Salakhutdinov, N.F., Khimiya v interesakh ustoichivogo razvitiya (Chemistry for Sustainable Development), 2010, no. 18, p. 457.Google Scholar
  25. 25.
    Volcho, K.P., Ilina, I.V., Salakhutdinov, N.F., and Anikeev, V.I., Arkivoc., 2011, vol. viii, p. 134.Google Scholar
  26. 26.
    Ardashov, O.V., Genaev, A.M., Il’ina, I.V., Korchagina, D.V., Volcho, K.P., and Salakhutdinov, N.F., Russ. J. Org. Chem., 2010, vol. 46, p. 1786.CrossRefGoogle Scholar
  27. 27.
    Pankratyev, E.Yu., Tulyabaev, A.R., and Khalilov, L.M., J. Comp. Chem., 2011, vol. 32, p. 2055.CrossRefGoogle Scholar
  28. 28.
    Ardashov, O.V., Zarubaev, V.V., Shtro, A.A., Korchagina, D.V., Volcho, K.P., Salakhutdinov, N.F., and Kiselev, O.I., Lett. Drug Design & Discovery, 2011, vol. 8, p. 375.Google Scholar
  29. 29.
    Holland, H.L., Popperl, H., Ninniss, R.W., and Chenchaiah, P.C., Can. J. Chem., 1985, vol. 63, p. 1118.CrossRefGoogle Scholar
  30. 30.
    Sugimoto, T., Kokubo, T., Miyazaki, J., Tanimoto, S., and Okano, M., Chem. Commun., 1979, p. 402.Google Scholar
  31. 31.
    Imre, G., Jakli, I., Kalaszi, A., and Farkas, O., Advanced Automatic Generation of 3D Molecular Structures, 1st European Chemistry Congress, Budapest, Hungary, 27–31, August, 2006.Google Scholar
  32. 32.
    Chang, C. and Gilson, M.K., J. Comput. Chem., 2003, vol. 24, p. 1987.CrossRefGoogle Scholar
  33. 33.
    Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.CrossRefGoogle Scholar
  34. 34.
    Laikov, D.N., Chem. Phys. Lett., 2005, 416, p. 116.CrossRefGoogle Scholar
  35. 35.
    Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151; Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., 2005, p. 820.CrossRefGoogle Scholar
  36. 36.
    Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Barkhash, V.A., and Salakhutdinov, N.F., Helv. Chim. Acta, 2007, vol. 90, p. 353.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • I. V. Il’ina
    • 1
  • E. A. Koneva
    • 1
  • D. V. Korchagina
    • 1
  • G. E. Sal’nikov
    • 1
  • A. M. Genaev
    • 1
  • K. P. Volcho
    • 1
    Email author
  • N. F. Salakhutdinov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia

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