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Russian Chemical Bulletin

, Volume 55, Issue 12, pp 2187–2189 | Cite as

[(1S)-endo]-(−)-borneol-tethered oxazoline phosphite as a P,N-bidentate ligand in palladium-catalyzed enantioselective allylic amination

  • E. B. Benetsky
  • A. S. Safronov
  • T. B. Grishina
  • P. V. Petrovskii
  • V. A. Davankov
  • K. N. Gavrilov
Article

Abstract

P,N-Bidentate oxazoline phosphite containing an acyclic phosphorus center with [(1S)-endo]-(−)-borneol fragments and its palladium chelate complex [Pd(η-C3H5)(η2-P,N)]BF4 were synthesized for the first time. The use of this new ligand in Pd-catalyzed asymmetric amination of 1,3-diphenylpropenyl acetate with pyrrolidine afforded the product with 86% ee.

Key words

chiral phosphites ligands palladium complexes asymmetric amination metal complex catalysis asymmetric synthesis 

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References

  1. 1.
    K. N. Gavrilov, O. G. Bondarev, and A. I. Polosukhin, Usp. Khim., 2004, 73, 726 [Russ. Chem. Rev., 2004, 73, 671 (Engl. Transl.)].CrossRefGoogle Scholar
  2. 2.
    P. J. Guiry and C. P. Saunders, Adv. Synth. Catal., 2004, 346, 497.CrossRefGoogle Scholar
  3. 3.
    R. Pretot and A. Pfaltz, Angew. Chem., Int. Ed., 1998, 37, 323.CrossRefGoogle Scholar
  4. 4.
    A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Hormann, S. McIntyre, F. Menges, M. Schonleber, S. P. Smidt, B. Wustenberg, and N. Zimmermann, Adv. Synth. Catal., 2003, 345, 33.CrossRefGoogle Scholar
  5. 5.
    Y. Mata, M. Dieguez, O. Pamies, and C. Claver, Adv. Synth. Catal., 2005, 347, 1943.CrossRefGoogle Scholar
  6. 6.
    R. Hilgraf and A. Pfaltz, Adv. Synth. Catal., 2005, 347, 61.CrossRefGoogle Scholar
  7. 7.
    K. N. Gavrilov, V. N. Tsarev, S. I. Konkin, S. E. Lyubimov, A. A. Korlyukov, M. Yu. Antipin, and V. A. Davankov, Eur. J. Inorg. Chem., 2005, 3311.Google Scholar
  8. 8.
    K. N. Gavrilov, V. N. Tsarev, S. V. Zheglov, S. E. Lyubimov, A. A. Shyryaev, P. V. Petrovskii, and V. A. Davankov, Mendeleev Commun., 2004, 260.Google Scholar
  9. 9.
    O. G. Bondarev, S. E. Lyubimov, A. A. Shiryaev, N. E. Kadilnikov, V. A. Davankov, and K. N. Gavrilov, Tetrahedron: Asymmetry, 2002, 13, 1587.CrossRefGoogle Scholar
  10. 10.
    A. V. Korostylev, O. G. Bondarev, A. Yu. Kovalevsky, P. V. Petrovskii, V. A. Davankov, and K. N. Gavrilov, Inorg. Chim. Acta, 2001, 312, 117.CrossRefGoogle Scholar
  11. 11.
    K. N. Gavrilov, I. S. Mikhel’, K. A. Lyssenko, M. Yu. Antipin, G. I. Timofeeva, A. I. Polosukhin, and A. V. Korostylev, Zh. Neorg. Khim., 1997, 42, 593 [Russ. J. Inorg. Chem., 1997, 42, 520 (Engl. Transl.)].Google Scholar
  12. 12.
    D. Smyth, H. Tye, C. Eldred, N. W. Alcock, and M. Wills, J. Chem. Soc., Perkin Trans. 1, 2001, 2840.Google Scholar
  13. 13.
    H. Yang, M. A. Khan, and K. M. Nicholas, Organometallics, 1993, 12, 3485.CrossRefGoogle Scholar
  14. 14.
    P. R. Auburn, P. B. McKenzie, and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033.CrossRefGoogle Scholar
  15. 15.
    K. N. Gavrilov, O. G. Bondarev, V. N. Tsarev, A. A. Shiryaev, S. E. Lyubimov, A. S. Kucherenko, and V. A. Davankov, Izv. Akad. Nauk, Ser. Khim., 2003, 116 [Russ. Chem. Bull., Int. Ed., 2003, 52, 122].Google Scholar
  16. 16.
    V. N. Tsarev, S. I. Konkin, A. A. Shyryaev, V. A. Davankov, and K. N. Gavrilov, Tetrahedron: Asymmetry, 2005, 16, 1737.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • E. B. Benetsky
    • 1
  • A. S. Safronov
    • 2
  • T. B. Grishina
    • 2
  • P. V. Petrovskii
    • 1
  • V. A. Davankov
    • 1
  • K. N. Gavrilov
    • 2
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.S. A. Esenin Ryazan State UniversityRyazanRussian Federation

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