Skip to main content
SpringerLink
Log in

Asymmetric oxidation of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole

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

Abstract

Both enantiomers of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole 1-oxide as analogs of Varacins B and C were synthesized for the first time. The use of the Modena method ensures higher optical purity but lower yields of the chiral sulfoxides, as compared to the Kagan procedure.

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. Jacob, C., Nat. Prod. Rep., 2006, vol. 23, p. 851.

    Article  CAS  Google Scholar 

  2. Makarieva, T.N., Stonik, V.A., Dmitrenok, A.S., Grebnev, B.B., Isakov, V.V., Rebachyk, N.M., and Rashkes, Y.W., J. Nat. Prod., 1995, vol. 58, p. 254.

    Article  CAS  Google Scholar 

  3. Lee, A.H.F., Chen, J., Liu, D., Leung, T.Y., Chan, A.S., and Li, T., J. Am. Chem. Soc., 2002, vol. 124, p. 13 972.

    CAS  Google Scholar 

  4. Lee, A.H.F., Chan, A.S.C., and Li, T., Bioorg. Med. Chem. Lett., 2002, vol. 12, p. 3259.

    Article  CAS  Google Scholar 

  5. Bentley, R., Chem. Soc. Rev., 2005, vol. 34, p. 609.

    Article  CAS  Google Scholar 

  6. Volcho, K.P., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. J. Org. Chem., 2003, vol. 39, p. 1537.

    Article  CAS  Google Scholar 

  7. Kimura, T., Hanzawa, M., Tsujimura, K., Takahashi, T., Kawai, Y., Horn, E., Fujii, T., Ogawa, S., and Sato, R., Bull. Chem. Soc. Jpn., 2002, vol. 75, p. 817.

    Article  CAS  Google Scholar 

  8. Yagupol’skii, L.M. and Mospan, V.S., Ukr. Khim. Zh., 1955, vol. 21, p. 81.

    Google Scholar 

  9. Rasheed, K. and Warkenstein, J.D., FRG Patent Appl. no. 2 644 036, 1977; Chem. Abstr., 1977, vol. 87, no. 53 253.

  10. Rasheed, K. and Warkentin, J.D., US Patent no. 4 084 954, 1978; Chem. Abstr., 1979, vol. 90, no. 168 611.

  11. Rasheed, K. and Warkentin, J.D., J. Org. Chem., 1979, vol. 44, p. 267.

    Article  CAS  Google Scholar 

  12. Rasheed, K. and Warkentin, J.D., J. Org. Chem., 1980, vol. 45, p. 4806.

    Article  CAS  Google Scholar 

  13. Bolm, C. and Bienewald, F., Angew. Chem., Int. Ed. Engl., 1995, vol. 34, p. 2640.

    Article  CAS  Google Scholar 

  14. Pitchen, P., Dunach, T., Desmukh, N.N., and Kagan, H.B., J. Am. Chem. Soc., 1984, vol. 106, p. 8188.

    Article  CAS  Google Scholar 

  15. Di Furia, F., Modena, G., and Seraglia, R., Synthesis, 1984, p. 325.

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    T. M. Khomenko, D. V. Korchagina, K. P. Volcho & N. F. Salakhutdinov

Authors
  1. T. M. Khomenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Korchagina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. P. Volcho
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. F. Salakhutdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. P. Volcho.

Additional information

Original Russian Text © T.M. Khomenko, D.V. Korchagina, K.P. Volcho, N.F. Salakhutdinov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 9, pp. 1415–1417.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khomenko, T.M., Korchagina, D.V., Volcho, K.P. et al. Asymmetric oxidation of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole. Russ J Org Chem 45, 1402–1404 (2009). https://doi.org/10.1134/S1070428009090140

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009090140

Keywords

Search

Navigation