Skip to main content
SpringerLink
Log in

Asymmetric induction in reactions of chiral acylazinium salts (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The effectiveness of asymmetric induction in the reactions of chiral acylazinium salts produced from pyridines, quinolines, isoquinolines, 1,2,4-triazinones, and a series of chiral acylating agents is analyzed.

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. D. L. Comins and S. P. Joseph, in: C. J. Moody (editor), Advances in Nitrogen Heterocycles, Vol. 2, JAI Press, Greenwich (1996), p. 251.

    Chapter  Google Scholar 

  2. D. L. Comins and S. P. Joseph, in: A. McKillop (editor), Comprehensive Heterocyclic Chemistry II, Pergamon Press, Oxford (1996), Vol. 5, p. 37.

  3. D. L. Comins, J. Heterocycl. Chem., 36, 1491 (1999).

    Article  CAS  Google Scholar 

  4. J. T. Kuethe and D. L. Comins, J. Org. Chem., 69, 2863 (2004).

    Article  CAS  Google Scholar 

  5. J. T. Kuethe and D. L. Comins, J. Org. Chem., 69, 5219 (2004).

    Article  CAS  Google Scholar 

  6. D. L. Comins, J. T. Kuethe, T. M. Miller, F. C. Février, and C. A. Brooks, J. Org. Chem., 70, 5221 (2005).

    Article  CAS  Google Scholar 

  7. I. N. Egorov, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Usp. Khim., 74, 1176 (2005). [Russ. Chem. Rev., 74, 1073 (2005)].

    Article  Google Scholar 

  8. J. A. Bull, J. J. Mousseau, G. Pelletier, and A. B. Charette, Chem. Rev., 112, 2642 (2012).

    Article  CAS  Google Scholar 

  9. M. Ahamed and M. H. Todd, Eur. J. Org. Chem., 5935 (2010).

  10. J. Bräckow, J. Pabel, P. Mayer, K. Polborn, and K. T. Wanner, Tetrahedron, 66, 7279 (2010).

    Article  Google Scholar 

  11. M. Pauvert, S. C. Collet, M.-J. Bertrand, A. Y. Guingant, and M. Evain, Tetrahedron Lett., 46, 2983 (2005).

    Article  CAS  Google Scholar 

  12. P. Hermange, M. E. T. H. Dau, P. Retailleau, and R. H. Dodd, Org. Lett., 11, 4044 (2009).

    Article  CAS  Google Scholar 

  13. O. Sieck, M. Ehwald, and J. Liebscher, Eur. J. Org. Chem., 663 (2005).

  14. C. Bender and J. Liebscher, ARKIVOC, vi, 111 (2009).

  15. H. W. Gibson, M. A. G. Berg, J. C. Dickson, P. R. Lecavalier, H. Wang, and J. S. Merola, J. Org. Chem., 72, 5759 (2007).

    Article  CAS  Google Scholar 

  16. C. Fuchs, C. Bender, B. Ziemer, and J. Liebscher, J. Heterocycl. Chem., 45, 1651 (2008).

    Article  CAS  Google Scholar 

  17. D. B. Gotchev and D. L. Comins, J. Org. Chem., 71, 9393 (2006).

    Article  CAS  Google Scholar 

  18. D. L. Comins and J. J. Sahn, Org. Lett., 7, 5227 (2005).

    Article  CAS  Google Scholar 

  19. B. H. Wolfe, A. H. Libby, R. S. Al-Awar, C. J. Foti, and D. L. Comins, J. Org. Chem., 75, 8564 (2010).

    Article  CAS  Google Scholar 

  20. M. M. Martínez, L. A. Sarandeses, and J. P. Sestelo, Tetrahedron Lett., 48, 8536 (2007).

    Article  Google Scholar 

  21. I. N. Egorov, G. V. Zyryanov, E. N. Ulomsky, V. L. Rusinov, and O. N. Chupakhin, Tetrahedron Lett., 47, 7485 (2006).

    Article  CAS  Google Scholar 

  22. O. N. Chupakhin, I. N. Egorov, V. L. Rusinov, and P. A. Slepukhin, Izv. Akad. Nauk, Ser. Khim., 970 (2010). [Russ. Chem. Bull., 59, 991 (2010)].

    Google Scholar 

  23. I. N. Egorov, O. N. Chupakhin, M. V. Berezin, G. L. Rusinov, V. L. Rusinov, E. V. Buravlev, I. Yu. Chukicheva, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 893 (2011). [Russ. Chem. Bull., 60, 893 (2011)].

    Google Scholar 

  24. I. N. Egorov, B. König, V. L. Rusinov, and O. N. Chupakhin, Mendeleev Commun., 18, 99 (2008).

    Article  CAS  Google Scholar 

  25. P. Bharathi and D. L. Comins, Org. Lett., 10, 221 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    I. N. Egorov, V. L. Rusinov & O. N. Chupakhin

  2. I. Ya. Postovskii Institute of Organic Synthesis, 22 S. Kovalevskoi St./ 20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    V. L. Rusinov & O. N. Chupakhin

Authors
  1. I. N. Egorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. N. Egorov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 736-749, May, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Egorov, I.N., Rusinov, V.L. & Chupakhin, O.N. Asymmetric induction in reactions of chiral acylazinium salts (Review). Chem Heterocycl Comp 48, 684–697 (2012). https://doi.org/10.1007/s10593-012-1046-7

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1046-7

Keywords

Search

Navigation