Skip to main content
SpringerLink
Log in

Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Brunner, H., Riepl, G., and Weitzer, H., Angew. Chem. Int. Ed., 1983, vol. 22, no. 4, p. 331.

    Article  Google Scholar 

  2. Brunner, H., Becker, R., and Riepl, G., Organometallics, 1984, vol. 3, no. 9, p. 1354.

    Article  CAS  Google Scholar 

  3. Brunner, H. and Kürzinger, A., J. Organomet. Chem., 1988, vol. 346, no. 3, p. 413.

    Article  CAS  Google Scholar 

  4. Lipshutz, B.H., Lower, A., and Noson, K., Org. Lett., 2002, vol. 4, no. 23, p. 4045.

    Article  CAS  Google Scholar 

  5. Lipshutz, B.H., Lower, A., Kucejko, R.J., and Noson, K., Org. Lett., 2006, vol. 8, no. 14, p. 2969.

    Article  CAS  Google Scholar 

  6. Comte, V., Balan, C., Le Gendre, P., and Moïse, C., Chem. Comm., 2007, no. 7, p. 713.

  7. Riemcshneider, R. and Hoyer, G.-A., Z. Naturforschg. B, 1962, vol. 17, nos. 11–12, p. 765.

    Google Scholar 

  8. Vos, O., Budke, L., Fatome, M., and Hooidonk, C., Int. J. Radiat. Biol., 1981, vol. 39, no. 3, p. 291.

    Article  CAS  Google Scholar 

  9. Nagasawa, H., Goon, D., Muldoon, W., and Zera, R., J. Med. Chem., 1984, vol. 27, no. 5, p. 591.

    Article  CAS  Google Scholar 

  10. Roberts, J., Amino Acids, 1995, vol. 8, no. 2, p. 113.

    Article  CAS  Google Scholar 

  11. Gyoergydeak, Z., Kajtar-Peredy, M., Kajtar, J., and Kajtar, M., Liebigs Ann. Chem., 1987, no. 11, p. 927.

  12. Braibante, M.E.F., Braibante, H.S., and Costenaro, E.R., Synthesis, 1999, no. 6, p. 943.

  13. Soloway, H., Kipnis, F, Ornfelt, J., and Spoerri, P.E., J. Am. Chem. Soc., 1948, vol. 70, no. 4, p. 1667.

    Article  CAS  Google Scholar 

  14. Brunner, H. and Obermann, U., Chem. Ber., 1989, vol. 122, no. 3, p. 499.

    Article  CAS  Google Scholar 

  15. Gunther, H., Vvedenie v kurs spektroskopii YaMR (Introduction to NMR Spectroscopy), Moscow: Mir, 1984.

    Google Scholar 

  16. Parthasarathy, R., Paul, B., and Korytnyk, W., J. Am. Chem. Soc., 1976, vol. 98, no. 21, p. 6634.

    Article  CAS  Google Scholar 

  17. Braga, A.L., Appelt, H.R., Schneider, P.H., Rodrigues, O.E.D., Silveira, C.C., and Wessjohann, L.A., Tetrahedron, 2001, vol. 57, no. 16, p. 3291.

    Article  CAS  Google Scholar 

  18. Ojima, I., Li, Z., and Zhu, J., The Chemistry of Organic Silicon Compounds, Rappaport, Z. and Apeloig, Y., Eds., New York: Wiley, 1998, vol. 2, part 2, p. 1687.

    Chapter  Google Scholar 

  19. Perspektivy gidrosililirovania (Hydrosilylation Prospects), Lukevits, E., Ed., Riga: Inst. Org. Sinteza Latv. Akad. Nauk, 1992.

    Google Scholar 

  20. Marciniec, B., Maciejewski, H., Pietraszuk, C., and Pawluć, P., Advances in Silicon Science, Marciniec, B., Ed., Springer, 2009, vol. 1.

  21. Uvarov, V.M., de Vekki, D.A., Reshetilovskii, V.P., and Skvortsov, N.K., Zh. Obshch. Khim., 2010, vol. 80, no. 1, p. 39.

    Google Scholar 

  22. Brunner, H. and Obermann, U., Chem. Ber., 1989, vol. 122, no. 3, p. 499.

    Article  CAS  Google Scholar 

  23. Gemperline, P., Practical Guide to Chemometrics, New York: Taylor and Francis, 2006.

    Book  Google Scholar 

  24. Takeuchi, Y., Noriaki, I., Satoh, T., Koizumi, T., and Yamaguchir, K., J. Org. Chem., 1993, vol. 58, no. 7, p. 1812.

    Article  CAS  Google Scholar 

  25. Rukovodstvo po neorganicheskomu sintezu (Inorganic Synthesis Guidelines), Brauer, E., Ed., Moscow: Mir, 1986, vol. 6, p. 1867.

    Google Scholar 

  26. Braga, A.L., Appelt, H.R., Schneider, P.H., Silveira, C.C., and Wessjohann, L.A., Tetrahedron: Asymmetry, 1999, vol. 10, no. 9, p. 1733.

    Article  CAS  Google Scholar 

  27. Takeuchi, Y., Noriaki, I., Satoh, T., Koizumi, T., and Yamaguchir, K., J. Org. Chem., 1993, vol. 58, no. 7, p. 1812.

    Article  CAS  Google Scholar 

  28. Laszlo, S., Liebigs Ann. Chem., 1985, no. 4, p. 657.

  29. Oya, M., Ito, S., Harada, K.-I., Suzuki, M., and Tatematsu, A., Chemical & Pharmaceutical Bulletin, 1982, vol. 30, no. 2, p. 2705.

    CAS  Google Scholar 

  30. Szilagyi, L. and Gyorgydeak, Z., J. Am. Chem. Soc., 1979, vol. 101, no. 2, p. 427.

    Article  CAS  Google Scholar 

  31. Howard-Lock, H.E., Lock, C. J. L., and Martins, M.L., Can. J. Chem., 1991, vol. 69, no. 11, p. 1721.

    Article  CAS  Google Scholar 

  32. Nagasawa, H.T., Goon, D.J.W., Muldoon, W.P., and Zera, R.T., J. Med. Chem., 1984, vol. 27, no. 5, p. 591.

    Article  CAS  Google Scholar 

  33. Confalone, P.N., Pizzolato, G., Baggiolini, E.G., Lollar, D., and Uskokovic, M.R., J. Am. Chem. Soc., 1977, vol. 99, no. 21, p. 7020.

    Article  CAS  Google Scholar 

  34. Sutcliffe, O.B., Storr, R.C., Gilchrist, T.L., and Rafferty, P., J. Chem. Soc., Perkin Trans. 1, 2001, no. 15, p. 1795.

  35. Schmolka, I.R. and Spoerri, P.E., J. Org. Chem., 1957, vol. 22, no. 8, p. 943.

    Article  CAS  Google Scholar 

  36. Terol, A., Fernandez, J.-P., Robbe, Y., Chapat, J.-P., Granger, R., and Sentenac-Roumanou, H., Eur. J. Med. Chem., 1978, vol. 13, no. 2, p. 153.

    CAS  Google Scholar 

  37. Kasida, Y. and Yakugaku, Z., C.A., 1950, vol. 44, nos. 4–6, p. 1490a.

    Google Scholar 

  38. Gududuru, V., Hurh, E., Dalton, J. T., and Miller, D.D., J. Med. Chem., 2005, vol. 48, no. 8, p. 2584.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Polytechnic University, St. Petersburg, Russia

    A. N. Skvortsov

  2. St. Petersburg State Technological Institute, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    V. M. Uvarov, D. A. de Vekki, E. P. Studentsov & N. K. Skvortsov

Authors
  1. A. N. Skvortsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. M. Uvarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. A. de Vekki
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. P. Studentsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. K. Skvortsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © A.N. Skvortsov, V.M. Uvarov, D.A. de Vekki, E.P. Studentsov, N.K. Skvortsov, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 10, pp. 1697–1711.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Skvortsov, A.N., Uvarov, V.M., de Vekki, D.A. et al. Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane. Russ J Gen Chem 80, 2007–2021 (2010). https://doi.org/10.1134/S107036321010021X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036321010021X

Keywords

Search

Navigation