A new and convenient approach for the synthesis of P-stereogenic intermediates bearing a tert-butyl(methyl)phosphino group

Abstract

Chiral organophosphorus compounds possessing a P-stereogenic center have been widely used as agricultural chemicals, pharmaceuticals, organocatalysts, and ligands for transition-metal catalysis. P-Stereogenic intermediates bearing a tert-butyl(methyl)phosphino group are important for the preparation of several commonly used diphosphine ligands. However, previously reported synthetic methods used hazardous starting materials and are difficult to operate. In order to overcome these limitations, a new and convenient synthesis for a number of P-stereogenic intermediates possessing a tert-butyl(methyl)phosphino group has been developed. The reported route relies on an air- and moisture-stable secondary phosphine oxide prepared from a readily available starting material, trichlorophosphane.

This is a preview of subscription content, access via your institution.

Fig. 1
Scheme 1

References

  1. 1.

    J.S. Harvey, V. Gouverneur, Chem. Commun. 46, 7477 (2010)

    CAS  Article  Google Scholar 

  2. 2.

    N. Oka, T. Wada, Chem. Soc. Rev. 40, 5829 (2011)

    CAS  Article  Google Scholar 

  3. 3.

    O.I. Kolodiazhnyi, Tetrahedron Asymmetry 23, 1 (2012)

    CAS  Article  Google Scholar 

  4. 4.

    Q. Yao, A. Wang, J. Pu, Y. Tang, Chin. J. Org. Chem. 34, 292 (2014)

    CAS  Article  Google Scholar 

  5. 5.

    M. Dutartre, J. Bayardon, S. Jugé, Chem. Soc. Rev. 45, 5771 (2016)

    CAS  Article  Google Scholar 

  6. 6.

    W.S. Knowles, M.J. Sabacky, B.D. Vineyard, D.J. Weinkauff, J. Am. Chem. Soc. 97, 2567 (1975)

    CAS  Article  Google Scholar 

  7. 7.

    A. Grabulosa, P-Stereogenic ligands in enantioselective catalysis (The Royal Society of Chemistry, Cambridge, 2010)

    Google Scholar 

  8. 8.

    T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 120, 1635 (1998)

    CAS  Article  Google Scholar 

  9. 9.

    Y. Yamanoi, T. Imamoto, J. Org. Chem. 64, 2988 (1999)

    CAS  Article  Google Scholar 

  10. 10.

    H.-P. Wu, G. Hoge, Org. Lett. 6, 3645 (2004)

    CAS  Article  Google Scholar 

  11. 11.

    T. Imamoto, K. Sugita, K. Yoshida, J. Am. Chem. Soc. 127, 11934 (2005)

    CAS  Article  Google Scholar 

  12. 12.

    Y. Yamamoto, T. Koizumi, K. Katagiri, Y. Furuya, H. Danjo, T. Imamoto, K. Yamaguchi, Org. Lett. 8, 6103 (2006)

    CAS  Article  Google Scholar 

  13. 13.

    I.D. Gridnev, T. Imamoto, G. Hoge, M. Kouchi, H. Takahahsi, J. Am. Chem. Soc. 130, 2560 (2008)

    CAS  Article  Google Scholar 

  14. 14.

    M. Revés, C. Ferrer, T. León, S. Doran, P. Etayo, A. Vidal-Ferran, A. Riera, X. Verdaguer, Angew. Chem. Int. Ed. 49, 9452 (2010)

    Article  Google Scholar 

  15. 15.

    K. Tamura, M. Sugiya, K. Yoshida, A. Yanagisawa, T. Imamoto, Org. Lett. 12, 4400 (2010)

    CAS  Article  Google Scholar 

  16. 16.

    T. Imamoto, K. Tamura, Z. Zhang, Y. Horiuchi, M. Sugiya, K. Yoshida, A. Yanagisawa, I.D. Gridnev, J. Am. Chem. Soc. 134, 1754 (2012)

    CAS  Article  Google Scholar 

  17. 17.

    Z. Zhang, K. Tamura, D. Mayama, M. Sugiya, T. Imamoto, J. Org. Chem. 77, 4184 (2012)

    CAS  Article  Google Scholar 

  18. 18.

    B. Ding, Z. Zhang, Y. Xu, Y. Liu, M. Sugiya, T. Imamoto, W. Zhang, Org. Lett. 15, 5476 (2013)

    CAS  Article  Google Scholar 

  19. 19.

    Q. Hu, Z. Zhang, Y. Liu, T. Imamoto, W. Zhang, Angew. Chem. Int. Ed. 54, 2260 (2015)

    CAS  Article  Google Scholar 

  20. 20.

    Z. Yang, C. Xia, D. Liu, Y. Liu, M. Sugiya, T. Imamoto, W. Zhang, Org. Biomol. Chem. 13, 2694 (2015)

    CAS  Article  Google Scholar 

  21. 21.

    Z. Yang, D. Liu, Y. Liu, M. Sugiya, T. Imamoto, W. Zhang, Organometallics 34, 1228 (2015)

    CAS  Article  Google Scholar 

  22. 22.

    Z. Yang, X. Wei, D. Liu, Y. Liu, M. Sugiya, T. Imamoto, W. Zhang, J. Organomet. Chem. 791, 41 (2015)

    CAS  Article  Google Scholar 

  23. 23.

    Y. Xu, Z. Yang, B. Ding, D. Liu, Y. Liu, M. Sugiya, T. Imamoto, W. Zhang, Tetrahedron 71, 6832 (2015)

    CAS  Article  Google Scholar 

  24. 24.

    Z. Zhang, Q. Hu, Y. Wang, J. Chen, W. Zhang, Org. Lett. 17, 5380 (2015)

    CAS  Article  Google Scholar 

  25. 25.

    Q. Hu, J. Chen, Z. Zhang, Y. Liu, W. Zhang, Org. Lett. 18, 1290 (2016)

    CAS  Article  Google Scholar 

  26. 26.

    D. Fan, J. Lu, Y. Liu, Z. Zhang, Y. Liu, W. Zhang, Tetrahedron 72, 5541 (2016)

    CAS  Article  Google Scholar 

  27. 27.

    Q. Hu, Y. Hu, Y. Liu, Z. Zhang, Y. Liu, W. Zhang, Chem. Eur. J. (2016). doi:10.1002/chem.201604298

    Google Scholar 

  28. 28.

    K. Yao, D. Liu, Q. Yuan, T. Imamoto, Y. Liu, W. Zhang, Org. Lett. 18, 6296 (2016)

    CAS  Article  Google Scholar 

  29. 29.

    L. Ackermann, R. Vicente, N. Hofmann, Org. Lett. 11, 4274 (2009)

    CAS  Article  Google Scholar 

  30. 30.

    A.J. Bloomfield, J.M. Qian, S.B. Herzon, Organometallics 29, 4193 (2010)

    CAS  Article  Google Scholar 

  31. 31.

    D. Gatineau, L. Giodano, G. Buono, J. Am. Chem. Soc. 133, 10728 (2011)

    CAS  Article  Google Scholar 

  32. 32.

    L. Copey, L. Jean-Gérard, B. Andrioletti, E. Framery, Tetrahedron Lett. 57, 543 (2016)

    CAS  Article  Google Scholar 

  33. 33.

    T. Imamoto, K. Tamura, T. Ogura, Y. Ikematsu, D. Mayama, M. Sugiya, Tetrahedron Asymmetry 21, 1522 (2010)

    CAS  Article  Google Scholar 

  34. 34.

    T. Imamoto, T. Kusumoto, N. Suzuki, K. Sato, J. Am. Chem. Soc. 107, 5301 (1985)

    CAS  Article  Google Scholar 

  35. 35.

    K.V. Rajendran, D.G. Gilheany, Chem. Commun. 48, 817 (2012)

    CAS  Article  Google Scholar 

  36. 36.

    M. Stankevič, K.M. Pietrusiewicz, Synlett 2003, 1012 (2003)

    Google Scholar 

  37. 37.

    E. Salomó, S. Orgué, A. Riera, X. Verdaguer, Synthesis 48, 2569 (2016)

    Google Scholar 

Download references

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21572131). We gratefully acknowledge Prof. Tsuneo Imamoto and Dr. Masashi Sugiya for helpful discussion. We also thank the Instrumental Analysis Center of SJTU for characterization.

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Zhenfeng Zhang or Wanbin Zhang.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Liu, Y., Ding, B., Liu, D. et al. A new and convenient approach for the synthesis of P-stereogenic intermediates bearing a tert-butyl(methyl)phosphino group. Res Chem Intermed 43, 4959–4966 (2017). https://doi.org/10.1007/s11164-017-2923-6

Download citation

Keywords

  • P-stereogenic
  • Organophosphorus
  • Ligand
  • Phosphine borane
  • Secondary phosphine oxide