Russian Chemical Bulletin

, Volume 56, Issue 10, pp 2094–2096 | Cite as

P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions

  • S. E. Lyubimov
  • V. A. Davankov
  • P. V. Petrovskii
  • N. M. Loim
Article
Received:
Revised:

Abstract

A series of P-chiral monodentate diamidophosphite ligands of the 1,3-diaza-2-phosphabicyclo[3.3.0]octane family was tested in the Rh-catalyzed hydrogenation of dimethyl itaconate and addition of phenylboronic acid at the carbonyl group of trans-cinnamaldehyde. The enantioselectivities and conversions of these reactions are strongly dependent on the nature of the exo-cyclic substituent of the ligand.

Key words

1,3-diaza-2-phosphabicyclo[3.3.0]octanes P-chirality diamidophosphites metal complex catalysis rhodium complexes asymmetric hydrogenation phenylboronic acid trans-cinnamaldehyde 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. T. Reetz, J. Ma, and R. Goddard, Angew. Chem. Int. Ed., 2005, 3, 412.CrossRefGoogle Scholar
  2. 2.
    O. G. Bondarev and R. Goddard, Tetrahedron Lett., 2006, 47, 9013.CrossRefGoogle Scholar
  3. 3.
    V. N. Tsarev, S. E. Lyubimov, A. A. Shiryaev, S. V. Zheglov, O. G. Bondarev, V. A. Davankov, A. A. Kabro, S. K. Moiseev, V. N. Kalinin, and K. N. Gavrilov, Eur. J. Org. Chem., 2004, 2214.Google Scholar
  4. 4.
    S. E. Lyubimov, V. A. Davankov, and K. N. Gavrilov, Tetrahedron Lett., 2006, 47, 2721.CrossRefGoogle Scholar
  5. 5.
    S. E. Lyubimov, V. A. Davankov, M. G. Maksimova, P. V. Petrovskii, and K. N. Gavrilov, J. Mol. Catal. A: Chemical, 2006, 259, 183.CrossRefGoogle Scholar
  6. 6.
    J. M. Brunel, O. Legrand, S. Reymond, and G. Buono, J. Am. Chem. Soc., 1999, 121, 5807.CrossRefGoogle Scholar
  7. 7.
    M. Fontes, X. Verdaguer, L. Sola, M. A. Pericas, and A. Riera, J. Org. Chem., 2004, 69, 2532.CrossRefGoogle Scholar
  8. 8.
    H. Duan, J. Xie, W. Shi, Q. Zhang, and Q. Zhou, Org. Lett., 2006, 7, 1479.CrossRefGoogle Scholar
  9. 9.
    N. Loim, P. Kondrat’ev, N. Solov’eva, V. Antanovich, P. Petrovskii, Z. Parnes, and D. Kursanov, J. Organomet. Chem., 1981, 209, 233.CrossRefGoogle Scholar
  10. 10.
    G. Argouarch, O. Samuel, and H. B. Kagan, Eur. J. Org. Chem., 2000, 16, 2885.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • S. E. Lyubimov
    • 1
  • V. A. Davankov
    • 1
  • P. V. Petrovskii
    • 1
  • N. M. Loim
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations