Skip to main content
SpringerLink
Log in

Six-membered cyclic nitronates in the stereoselective synthesis of natural and bioactive compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In this report, the known strategies for the use of six-membered cyclic nitronates in directed organic synthesis are discussed.

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. For the first synthesis of six-membered cyclic nitronates 1, see: A. Risaliti, M. Forchiassin, and E. Valentin, Tetrahedron , 24, 1889 (1968).

  2. For the synthesis of six-membered cyclic nitronates by the cyclization of δ-halonitro compounds, see: I. E. Chlenov, V. I. Khudak, L. M. Kolymagina, N. S. Morozova, and V. A. Tartakovsky, Izv. AN SSSR, Ser. Khim., 1867 (1970). [Bull. Acad. Sci. USSR, 1757 (1970)].

  3. S. E. Denmark and A. Thorarensen, Chem. Rev., 96, 137 (1996).

    Article  CAS  Google Scholar 

  4. A. Yu Sukhorukov and S. L. Ioffe, Chem. Rev., 111, 5004 (2011).

    Article  Google Scholar 

  5. S. L. Ioffe, in: H. Feuer (editor), Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis: Novel Strategies in Synthesis, 2nd ed., Wiley, Hoboken (2008), p.435.

    Google Scholar 

  6. S. E. Denmark, Y.-C. Moon, and C. B. W. Senanayake, J. Am. Chem. Soc., 112, 311 (1990).

    Article  CAS  Google Scholar 

  7. S. E. Denmark and J. A. Dixon, J. Org. Chem., 63, 6167 (1998)

    Article  CAS  Google Scholar 

  8. S. E. Denmark, V. Guagnano, J. A. Dixon, and A. Stolle, J. Org. Chem., 62, 4610 (1997).

    Article  CAS  Google Scholar 

  9. S. E. Denmark, and L. Gomez, Org. Lett., 3, 2907 (2001).

    Article  CAS  Google Scholar 

  10. S. E. Denmark and E. A. Martinborough, J. Am. Chem. Soc., 121, 3046 (1999).

    Article  CAS  Google Scholar 

  11. S.E. Denmark and A. Thorarensen, J. Am. Chem. Soc., 119, 125 (1997).

    Article  CAS  Google Scholar 

  12. S. E. Denmark and L. R. Marcin, J. Org. Chem., 62, 1675 (1997).

    Article  CAS  Google Scholar 

  13. S. E. Denmark, J. I. Montgomery, and L. A. Kramps, J. Am. Chem. Soc., 128, 11620 (2006).

    Article  CAS  Google Scholar 

  14. M. S. Klenov, A. V. Lesiv, Yu. A. Khomutova, I. D. Nesterov, and S. L. Ioffe, Synthesis, 1159 (2004).

  15. A. A. Tishkov, A. V. Lesiv, Yu. A. Khomutova, Yu. A. Strelenko, I. D. Nesterov, M. Yu. Antipin S. L. Ioffe, and S. E. Denmark, J. Org. Chem., 68, 9477 (2003).

    Article  CAS  Google Scholar 

  16. A. Yu. Sukhorukov, M. S. Klenov, P. E. Ivashkin, A. V. Lesiv, Yu. A. Khomutova, and S. L. Ioffe, Synthesis, 97 (2007).

  17. O. L. Eliseev, P. E. Ivashkin, A. G. Ostapenko, A. V. Lesiv, Yu. A. Khomutova, S. L. Ioffe, and A. L. Lapidus, Synlett, 2239 (2006).

  18. A. A. Tabolin, A. V. Lesiv, and S. L. Ioffe, Synthesis, 3099 (2009).

  19. A. Yu. Sukhorukov, A. V. Lesiv, Yu. A. Khomutova, and S. L. Ioffe, Synthesis, 741 (2009).

  20. A. Yu. Sukhorukov, A. V. Lesiv, O. L. Eliseev, Yu, A. Khomutova, and S. L. Ioffe, Synthesis, 2570 (2009).

  21. A. Yu. Sukhorukov, S. O. Andryushkevich, G. G. Chilov, A. A. Zeifman, I. V. Svitanko, and S. L. Ioffe, Mendeleev. Commun., 21, 183 (2011).

    Article  CAS  Google Scholar 

  22. A. Yu. Sukhorukov, A. V. Lesiv, Yu. A. Khomutova, S. L. Ioffe, and V. A. Tartakovsky, Synthesis, 1999 (2009).

  23. P. A. Zhmurov, A. A. Tabolin, A. Yu. Sukhorukov, M. S. Klenov, A. V. Lesiv, S. L. Ioffe, and V. A. Tartakovsky, Izv. AN, Ser. Khim., 2243 (2011).

  24. A. Yu. Sukhorukov, A. V. Lesiv, Yu. A. Khomutova, S. L. Ioffe, and Yu. V. Khomutova, Synthesis 1205 (2008).

  25. A. Yu. Sukhorukov, Y. D. Boyko, Yu. A. Khomutova, Yu. V. Khomutova, Yu. V. Nelyubina, S. L. Ioffe, and V. A. Tartakovsky, J. Org. Chem., 76, 7893 (2011).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    A. Yu Sukhorukov, A. D. Dilman & S. L. Ioffe

Authors
  1. A. Yu Sukhorukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. D. Dilman
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. L. Ioffe
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. L. Ioffe.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, 54-59, January, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sukhorukov, A.Y., Dilman, A.D. & Ioffe, S.L. Six-membered cyclic nitronates in the stereoselective synthesis of natural and bioactive compounds. Chem Heterocycl Comp 48, 49–54 (2012). https://doi.org/10.1007/s10593-012-0968-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-0968-4

Keywords

Search

Navigation