SpringerLink
Log in

Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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. S. C. Bergmeier, Tetrahedron, 2000, 56, 2561.

    Article  CAS  Google Scholar 

  2. J. R. Huff, J. Med. Chem., 1991, 34, 2305.

    Article  CAS  Google Scholar 

  3. S. George, S. V. Narina, A. Sudalai, Tetrahedron, 2006, 39, 10202.

    Article  Google Scholar 

  4. S. Panev, A. Lindenb, V. Dimitrov, Tetrahedron Asymmetry, 2001, 12, 1313.

    Article  CAS  Google Scholar 

  5. D. Steiner, S. G. Sethofer, C. T. Goralski, B. Singaram, Tetrahedron Asymmetry, 2002, 13, 1477.

    Article  CAS  Google Scholar 

  6. Z. Szakonyi, T. Gonda, S. B. Ötvös, F. Fülöp, Tetrahedron Asymmetry, 2014, 25, 1138.

    Article  CAS  Google Scholar 

  7. Z. Szakonyi, K. Csillag, F. Fülöp, Tetrahedron Asymmetry, 2011, 22, 1021.

    Article  CAS  Google Scholar 

  8. Z. Szakonyi, A. Hetényi, F. Fülöp, Tetrahedron, 2008, 64, 1034.

    Article  CAS  Google Scholar 

  9. S. N. Joshi, S. V. Malhotra, Tetrahedron Asymmetry, 2003, 14, 1763.

    Article  CAS  Google Scholar 

  10. S. G. Zlotin, A. S. Kucherenko, I. P. Beletskaya, Russ. Chem. Rev. (Engl. Transl.), 2009, 78, 737.

    Article  CAS  Google Scholar 

  11. L. A. Paquette, R. J. Ross, Y.-J. Shi, J. Org. Chem., 1990, 55, 1589.

    Article  CAS  Google Scholar 

  12. W. Cocker, D. H. Grayson, Tetrahedron Lett., 1969, 51, 4451.

    Article  CAS  Google Scholar 

  13. F. Fringuelli, O. Piermatti, F. Pizzo, L. Vaccaro, J. Org. Chem., 1999, 64, 6094.

    Article  CAS  Google Scholar 

  14. C. Cimarelli, D. Fratoni, G. Palmieri, Tetrahedron Asymmetry, 2011, 22, 603.

    Article  CAS  Google Scholar 

  15. F. Fringuelli, F. Pizzo, L. Vaccaro, Synthesis, 2000, 5, 646.

    Article  Google Scholar 

  16. A. Malkov, M. Kabeshov, M. Bella, O. Kysilka, D. Malyshev, K. Pluháčková, P. Kočovský, Org. Lett., 2007, 9, 5473.aaa

    Article  CAS  Google Scholar 

  17. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9.

  18. G. M. Sheldrick. Acta Cryst., 2008, A64, p. 112.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167000, Syktyvkar, Russian Federation

    O. A. Banina, D. V. Sudarikov, L. L. Frolova & A. V. Kutchin

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. G. Nigmatov & S. G. Zlotin

  3. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    P. A. Slepukhin

Authors
  1. O. A. Banina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Sudarikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. G. Nigmatov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. L. Frolova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. A. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. G. Zlotin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. V. Kutchin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. A. Banina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0293—0296, February, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Banina, O.A., Sudarikov, D.V., Nigmatov, A.G. et al. Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone. Russ Chem Bull 66, 293–296 (2017). https://doi.org/10.1007/s11172-017-1730-y

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1730-y

Key words

Search

Navigation