Chemistry of Heterocyclic Compounds

, Volume 48, Issue 1, pp 73–81 | Cite as

Palladium-catalyzed carboamination in the synthesis of nitrogen-containing heterocycles

  • G. M. Belov
  • D. S. Belov
  • A. V. Kurkin
  • M. A. Yurovskaya
Article

An effective method for the stereoselective synthesis of various nitrogen-containing heterocycles by palladium-catalyzed carboamination is discussed. The method application examples to the synthesis of natural structures are presented.

Keywords

1,4-benzodiazepines morpholines palladium pyrrolidines compounds of tropane series cross-coupling stereoselective synthesis total synthesis 

References

  1. 1.
    L. S. Hegedus, G. F. Allen, and E. L. Waterman, J. Am. Chem. Soc., 98, 2674 (1976).CrossRefGoogle Scholar
  2. 2.
    R. I. McDonald, G. Liu, and S. S. Stahl, Chem. Rev., 111, 2981 (2011).CrossRefGoogle Scholar
  3. 3.
    M. M. Rogers, J. E. Wendlandt, I. A. Guzei, and S. S. Stahl, Org. Lett., 8, 2257 (2006).CrossRefGoogle Scholar
  4. 4.
    C. C. Scarborough and S. S. Stahl, Org. Lett., 8, 3251 (2006).CrossRefGoogle Scholar
  5. 5.
    G. Liu and S. S. Stahl, J. Am. Chem. Soc., 129, 6328 (2007).CrossRefGoogle Scholar
  6. 6.
    R. I. McDonald, P. B. White, A. B. Weinstein, C. P. Tam, and S. S. Stahl, Org. Lett., 13, 2830 (2011).CrossRefGoogle Scholar
  7. 7.
    J. P. Wolfe and M. A. Rossi, J. Am. Chem. Soc., 126, 1620 (2004).CrossRefGoogle Scholar
  8. 8.
    M. B. Hay, A. R. Hardin, and J. P. Wolfe, J. Org. Chem., 70, 3099 (2005).CrossRefGoogle Scholar
  9. 9.
    J. E. Ney and J. P. Wolfe, Angew. Chem., Int. Ed., 43, 3605 (2004).CrossRefGoogle Scholar
  10. 10.
    R. Lira and J. P. Wolfe, J. Am. Chem. Soc., 126, 13906 (2004)CrossRefGoogle Scholar
  11. 11.
    J. E. Ney, M. B. Hay, Q. Yang, and J. P. Wolfe, Adv. Synth. Catal., 347, 1614 (2005).CrossRefGoogle Scholar
  12. 12.
    Q. Yang, J. E. Ney, and J. P. Wolfe, Org. Lett., 7, 2575 (2005).CrossRefGoogle Scholar
  13. 13.
    M. B. Bertrand and J. P. Wolfe, Tetrahedron, 61, 6447 (2005).CrossRefGoogle Scholar
  14. 14.
    M. B. Bertrand, M. L. Leathen, and J. P. Wolfe, Org. Lett., 9, 457 (2007).CrossRefGoogle Scholar
  15. 15.
    B. R. Rosen, J. E. Ney, and J. P. Wolfe, J. Org. Chem., 75, 2756 (2010).CrossRefGoogle Scholar
  16. 16.
    J. S. Nakhla, J. W. Kampf, and J. P. Wolfe, J. Am. Chem. Soc., 128, 2893 (2006).CrossRefGoogle Scholar
  17. 17.
    M. B. Bertrand and J. P. Wolfe, Org. Lett., 9, 3073 (2007).CrossRefGoogle Scholar
  18. 18.
    M. B. Bertrand, J. D. Neukom, and J. P. Wolfe, J. Org. Chem., 73, 8851 (2008).CrossRefGoogle Scholar
  19. 19.
    J. D. Neukom, N. S. Perch, and J. P. Wolfe, Organometallics, 30, 1269 (2011).CrossRefGoogle Scholar
  20. 20.
    J. S. Nakhla and J. P. Wolfe, Org. Lett., 9, 3279 (2007).CrossRefGoogle Scholar
  21. 21.
    J. P. Wolfe, Synlett, 2913 (2008).Google Scholar
  22. 22.
    M. L. Leathen, B. R. Rosen, and J. P. Wolfe, J. Org. Chem.,74, 5107 (2009).CrossRefGoogle Scholar
  23. 23.
    A. F. Ward and J. P. Wolfe, Org. Lett., 13, 4728 (2011).CrossRefGoogle Scholar
  24. 24.
    J. D. Neukom, A. S. Aquino, and J. P. Wolfe, Org. Lett., 13, 2196 (2011).CrossRefGoogle Scholar
  25. 25.
    G. S. Lemen and J. P. Wolfe, Org. Lett., 12, 2322 (2010).CrossRefGoogle Scholar
  26. 26.
    D. M. Schultz and J. P. Wolfe, Org. Lett., 13, 2962 (2011).CrossRefGoogle Scholar
  27. 27.
    D. M. Schultz and J. P. Wolfe, Org. Lett., 12, 1028 (2010).CrossRefGoogle Scholar
  28. 28.
    G. S. Lemen and J. P. Wolfe, Org. Lett., 13, 3218 (2011).CrossRefGoogle Scholar
  29. 29.
    D. N. Mai and J. P. Wolfe, J. Am. Chem. Soc., 132, 12157 (2010).CrossRefGoogle Scholar
  30. 30.
    D. N. Mai, B. R. Rosen, and J. P. Wolfe, Org. Lett., 13, 2932 (2011).CrossRefGoogle Scholar
  31. 31.
    M. B. Bertrand and J. P. Wolfe, Org. Lett., 8, 2353 (2006).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • G. M. Belov
    • 1
  • D. S. Belov
    • 1
  • A. V. Kurkin
    • 1
  • M. A. Yurovskaya
    • 1
  1. 1.M. V. Lomonosov State UniversityMoscowRussia

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