Advertisement

Russian Chemical Bulletin

, Volume 61, Issue 1, pp 51–58 | Cite as

New bifunctional organocatalysts based on (R,R)-cyclohexane-1,2-diamine for the asymmetric addition of nucleophiles to aldehydes

  • V. I. Maleev
  • Z. T. Gugkaeva
  • A. T. Tsaloev
  • M. A. Moskalenko
  • V. N. Khrustalev
Full Articles

Abstract

The amide and sulfamide derivatives of (1R,2R)-N,N-diethylcyclohexane-1,2-diamine can serve as organocatalysts for addition of Me3SiCN and Et2Zn to aldehydes.

Key words

organocatalysis asymmetric synthesis aldehydes trimethylsilyl cyanide diethylzinc (R,R)-cyclohexane-1,2-diamine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res., 2008, 41, 655.CrossRefGoogle Scholar
  2. 2.
    Y. Wei, M. Shi, Acc. Chem. Res., 2010, 43, 1005.CrossRefGoogle Scholar
  3. 3.
    H. Pellissier, Tetrahedron, 2007, 63, 9267.CrossRefGoogle Scholar
  4. 4.
    W. Notz, F. Tanaka, C. Barbas III, Acc. Chem. Res., 2004, 37, 580.CrossRefGoogle Scholar
  5. 5.
    P. G. McGarraugh, S. E. Brenner, Tetrahedron, 2009, 65, 449.CrossRefGoogle Scholar
  6. 6.
    C. Wu, X. Fu, X. Ma, S. Li, Tetrahedron: Asymmetry, 2010, 20, 2465.CrossRefGoogle Scholar
  7. 7.
    T. Kanemitsu, A. Umehara, M. Miyazaki, K. Nagata, T. Itoh, Eur. J. Org. Chem., 2011, 993.Google Scholar
  8. 8.
    J. Aleman, Ch. B. Jacobsen, K. Frisch, J. Overgaard, K. A. Jørgensen, Chem. Commun., 2008, 632.Google Scholar
  9. 9.
    Ch. Y. Zhu, X. M. Deng, X. L. Sun, J. Ch. Zheng, Y. Tang, Chem. Commun., 2008, 738.Google Scholar
  10. 10.
    H. Pellissier, Tetrahedron, 2008, 64, 10279.CrossRefGoogle Scholar
  11. 11.
    D. Seebach, A. Beck, A. Heckel, Angew. Chem., Int. Ed., 2001, 40, 92.CrossRefGoogle Scholar
  12. 12.
    Yu. N. Belokon, V. I. Maleev, Z. T. Gugkaeva, M. A. Moskalenko, A. T. Tsaloev, A. S. Peregudov, S. Ch. Gagieva, K. A. Lyssenko, V. N. Khrustalev, A. V. Grachev, Izv. Akad. Nauk, Ser. Khim., 2007, 1451 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1507].Google Scholar
  13. 13.
    Y. N. Belokon, Z. T. Gugkaeva, V. I. Maleev, M. A. Moskalenko, M. North, A. T. Tsaloev, Tetrahedron: Asymmetry, 2010, 21, 1793.CrossRefGoogle Scholar
  14. 14.
    M. Nakajima, Y. Orito, T. Ishizuka, S. Hashimoto, Org. Lett., 2004, 6, 3763.CrossRefGoogle Scholar
  15. 15.
    T. Sakamoto, J. Itoh, K. Mori, T. Akiyama, Org. Biomol. Chem., 2010, 8, 5448.CrossRefGoogle Scholar
  16. 16.
    Y. N. Belokon, Z. T. Gugkaeva, V. I. Maleev, M. A. Moskalenko, A. T. Tsaloev, V. N. Khrustalev, K. V. Hakobyan, Tetrahedron: Asymmetry, 2011, 22, 167.CrossRefGoogle Scholar
  17. 17.
    S. Luo, H. Xu, J. Li, L. Zhang, J. P. Cheng, J. Am. Chem. Soc., 2007, 129, 3074.CrossRefGoogle Scholar
  18. 18.
    M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 4901.CrossRefGoogle Scholar
  19. 19.
    A. Berkessel, F. Cleemann, S. Mukherjee, T. Müller, J. Lex, Angew. Chem., Int. Ed., 2005, 44, 807.CrossRefGoogle Scholar
  20. 20.
    A. Berkessel, S. Mukherjee, T. N. Müller, F. Cleemann, K. Roland, M. Brandenburg, J. M. Neudörfl, J. Lex, Org. Biomol. Chem., 2006, 4, 4319.CrossRefGoogle Scholar
  21. 21.
    D. R. Li, A. He, J. R. Falck, Org. Lett., 2010, 12, 1756.CrossRefGoogle Scholar
  22. 22.
    A. Puglisi, M. Benaglia, R. Annunziata, D. Rossi, Tetrahedron: Asymmetry, 2008, 19, 2258.CrossRefGoogle Scholar
  23. 23.
    H. Yamamoto, K. Futatsugi, Angew. Chem., Int. Ed., 2005, 44, 1924.CrossRefGoogle Scholar
  24. 24.
    L. C. Bencze, C. Paizs, M. I. Tosa, E. Vass, F. D. Irimie, Tetrahedron: Asymmetry, 2010, 21, 443.CrossRefGoogle Scholar
  25. 25.
    R. Noyori, M. Kitamura, Angew. Chem., Int. Ed. Engl., 1991, 30.Google Scholar
  26. 26.
    P. Knochel, R. D. Singer, Chem. Rev., 1993, 93, 2117.CrossRefGoogle Scholar
  27. 27.
    S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc., 2007, 129, 15872.CrossRefGoogle Scholar
  28. 28.
    K. Soai, S. Niwa, Chem. Rev., 1992, 92, 833.CrossRefGoogle Scholar
  29. 29.
    M. T. Reetz, R. Steinbach, B. Wenderoth, Synth. Commun., 1981, 11, 261.CrossRefGoogle Scholar
  30. 30.
    J. M. Mithell, N. S. Finney, Tetrahedron: Lett., 2000, 41, 8431.CrossRefGoogle Scholar
  31. 31.
    G. M. Sheldrick, SADABS, v. 2.03, Bruker. Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2003.Google Scholar
  32. 32.
    G. M. Sheldrick, Acta Crystallogr., 2008, A64, 112.Google Scholar
  33. 33.
    J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, Ch. M. Zepp, J. Org. Chem., 1994, 59, 1939.CrossRefGoogle Scholar
  34. 34.
    F. Galsbøl, P. Steenbøl, B. S. Sørensen, Acta Chem. Scand., 1972, 26, 3605.CrossRefGoogle Scholar
  35. 35.
    S. E. Denmark, W. J. Chung, J. Org. Chem., 2006, 71, 4002.CrossRefGoogle Scholar
  36. 36.
    G. Zhao, X. G. Li, X. R. Wang, Tetrahedron: Asymmetry, 2001, 12, 399.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. I. Maleev
    • 1
  • Z. T. Gugkaeva
    • 1
  • A. T. Tsaloev
    • 1
  • M. A. Moskalenko
    • 1
  • V. N. Khrustalev
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations