Skip to main content
SpringerLink
Log in

Palladium(0)-catalyzed amination of allylic natural terpenic functionalized olefins

  • Research Article
  • Published:
Central European Journal of Chemistry

Abstract

The palladium(0) catalyzed amination of allylic acetates and carbonates derivatives from terpenic olefins was carried out under mild conditions. The reaction offers a very good method for the preparation of allylic amines and thus to provide a useful entry to new functionalized terpenic olefin products. The mechanism involving a formation of p-allyl-palladium intermediate complex is in good agreement with the results obtained with the optically active substrates, as well as via an analysis of the observed regio-and stereoselectivity.

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. M. Johannsen, K. A. Jorgensen, Chem. Rev. 98, 1689 (1998)

    Article  CAS  PubMed  Google Scholar 

  2. R. R. Rando, F. Bangerter, J. Am. Chem. Soc. 98, 6762 (1976)

    Article  CAS  PubMed  Google Scholar 

  3. C.Y.P. Teng, B. Ganem, Tetrahedron Lett. 23, 313 (1982)

    Article  CAS  Google Scholar 

  4. T. Kondo, H. Nakai, T. Goto, Tetrahedron. 29, 1801 (1973)

    Article  CAS  Google Scholar 

  5. B. M. Trost, J-P. Genêt, J. Am. Chem. Soc. 98, 8516 (1976)

    Article  CAS  Google Scholar 

  6. B. M. Trost, S. A. Godleski, J-P. Genêt, J. Am. Chem. Soc. 100, 3930 (1978)

    Article  CAS  Google Scholar 

  7. B. M. Trost, D. L. Van vranken, C. Bingel, J. Am. Chem. Soc. 114, 9327 (1992)

    Article  CAS  Google Scholar 

  8. T. Hayashi et al., J. Am. Chem Soc. 111, 6301 (1989)

    Article  CAS  Google Scholar 

  9. B. M. Trost, D. L. Van vranken, C. Bingel, J. Am. Chem. Soc. 115, 444 (1993)

    Article  CAS  Google Scholar 

  10. B. M. Trost, Angew. Chem. 101, 1199 (1989)

    Article  CAS  Google Scholar 

  11. T. Hayashi, In: I. Ojima (Ed.), Catalytic Asymmetric Synthesis (VCH, New York, 1993) 325

    Google Scholar 

  12. R. F. Heck, In: A. R. Katritzky, O. Meth-Cohen, C. W. Rees (Eds.), Palladium Reagents in Organic Syntheses (Academic Press, London, 1985) 2

    Google Scholar 

  13. A. Pfaltz, M. Lautens, In: E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis II (Springer, Berlin, 1999) 833

    Google Scholar 

  14. J. L. Malleron, J-C. Fiaud, J. Y. Legros, Handbook of Palladium Catalyzed Organic Reaction, (Academic Press, London, 1997)

    Google Scholar 

  15. Y. J. Shue, S. C. Yang, H. C. Lai, Tetrahedron Lett. 44, 1481 (2003)

    Article  CAS  Google Scholar 

  16. S. L. You, X. Z. Zhu, Y. M. Luo, X. L. Hou, L. X. Dai, J. Am. Chem. Soc. 123, 7471 (2001)

    Article  CAS  PubMed  Google Scholar 

  17. A. Fihri et al., Adv. Synth. Catal. 347, 1198 (2005)

    Article  CAS  Google Scholar 

  18. D. H. Nguyen et al., Appl. Organometal. Chem. 20, 845 (2006)

    Article  CAS  Google Scholar 

  19. L. Dubovyk, I. D. G. Watson, A. K. Yudin, J. Am. Chem. Soc. 129, 14172 (2007)

    Article  CAS  PubMed  Google Scholar 

  20. A. M. Johns; Z. Liu; J. F. Hartwig, Angew. Chem. Int. Ed. 46, 7259 (2007)

    Article  CAS  Google Scholar 

  21. W. H. Zheng, N. Sun, X. L. Hou, Org. Lett. 7, 5151 (2005)

    Article  CAS  PubMed  Google Scholar 

  22. B. M. Trost, M. L. Crawley, Chem. Rev. 103, 2921 (2003)

    Article  CAS  PubMed  Google Scholar 

  23. Z. Lu, S. Ma. Angew. Chem. Int. Ed. 47, 258 (2008)

    Article  CAS  Google Scholar 

  24. J. Muzart, Eur. J. Org. Chem. 3077 (2007)

  25. G. Muchow, J. M. Brunel, M. Maffei, D. Pardigon, G. Buono, Tetrahedron. 54, 10435. (1998)

    Article  Google Scholar 

  26. N. Uesaka, F. Saitoh, M. Mori, M. Shibasaki, K. Okamura, T. Date, J. Org. Chem. 59, 5633 (1994)

    Article  CAS  Google Scholar 

  27. Watanabe et al, J. Essent. Oil. Res. 9, 441 (1994)

    Article  Google Scholar 

  28. S. Elhoussame et al., J. Mol. Catal. A. 168, 15 (2001)

    Article  Google Scholar 

  29. H. Ziyat et al., Acta Chim. Slov. 51, 223 (2004)

    CAS  Google Scholar 

  30. L. Elfirdoussi et al., J. Mol. Catal. A. 135, 11 (1998)

    Article  CAS  Google Scholar 

  31. N. Fdil et al., J. Mol. Catal. A. 108, 15 (1996)

    Article  CAS  Google Scholar 

  32. J. A. Gonçalves, O. V. Howarth, E. V. Gusevskaya, J. Mol. Catal. A. 185, 97 (2002)

    Article  Google Scholar 

  33. M. J. Da Silva, J. A. Gonçalves, R. B. Alves, O. V. Howarth, E. V. Gusevskaya, J. Organomet. Chem. 689, 302 (2004)

    Article  Google Scholar 

  34. J. A. Gonçalves, E. V. Gusevskaya, Appl. Catal. A. 258, 93 (2004)

    Article  Google Scholar 

  35. A. J. Chalk, In: P. N. Rylander, H. Greenfield, R. L. Augustine (Eds.), Catalysis of Organic Reactions (Marcel Dekker, New York, 1988)

    Google Scholar 

  36. C. Chapuis, D. Jacoby, Appl. Catal. A. 212, 93 (2001)

    Article  Google Scholar 

  37. H. Mimoun, Chimia. 50, 620 (1996)

    Article  CAS  Google Scholar 

  38. R. D. Connell, T. Rein, B. Akermark, P. Helquist, J. Org. Chem. 53, 3845 (1998)

    Article  Google Scholar 

  39. B. M. Trost, E. Keinan, J. Am. Chem. Soc. 100, 7779 (1978)

    Article  CAS  Google Scholar 

  40. B. M. Trost, E. Keinan, J. Org. Chem. 44, 3451 (1979)

    Article  CAS  Google Scholar 

  41. J. Tsuji, K. Sato, H. Okumoto, J. Org. Chem. 8, 1341 (1984)

    Article  Google Scholar 

  42. B. M. Trost, D. L. Van vranken, Chem. Rev. 96, 395 (1996)

    Article  CAS  PubMed  Google Scholar 

  43. O. Piechaczyk, C. Thoumazet, Y. Jean, P. Le Floch, J. Am. Chem. Soc. 128, 14306 (2006)

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, Université Cadi Ayyad, BP 2390, Marrakech, Morocco

    Soufiane El Houssame, Larbi El Firdoussi & Abdellah Karim

  2. Département Sciences de la matière, Faculté Polydisciplinaire de Safi, Route Sidi bouzid, B.P 4162, Safi Université Cadi Ayyad, Morocco

    Hafid Anane

Authors
  1. Soufiane El Houssame
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hafid Anane
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Larbi El Firdoussi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Abdellah Karim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Soufiane El Houssame.

About this article

Cite this article

El Houssame, S., Anane, H., El Firdoussi, L. et al. Palladium(0)-catalyzed amination of allylic natural terpenic functionalized olefins. cent.eur.j.chem. 6, 470–476 (2008). https://doi.org/10.2478/s11532-008-0042-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-008-0042-3

Keywords

Search

Navigation