Skip to main content
SpringerLink
Log in

Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The synthesis of new P*-mono- and P*,N-bidentate diamidophosphites, containing 1,3,2-diazaphospholidine rings formed starting from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine, is described. Comparison of their efficiency in the Pd-catalyzed enantioselective allylation with (E)-1,3-diphenylallyl acetate showed that up to 97% ee was reached in the reaction involving dimethyl malonate as a C-nucleophile. The Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate gave up to 61% ee.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J. M. Brown, in Comprehensive Asymmetric Catalysis, Eds E. N. Jacobsen, A. Pfaltz, Y. Yamamoto, Springer, Berlin, 1999, Vol. 1, p. 121.

  2. T. Ohkuma, M. Kitamura, R. Noyori, in Catalytic Asymmetric Synthesis, Ed. I. Ojima, Wiley-VCH, New York, 2000, p. 1.

  3. M. J. Burk, Acc. Chem. Res., 2000, 33, 363.

    Article  CAS  Google Scholar 

  4. H.-U. Blaser, E. Schmidt, in Asymmetric Catalysis on Industrial Scale, Wiley-VCH, Weinheim, 2004.

    Google Scholar 

  5. I. P. Beletskaya, M. M. Kabachnik, Mendeleev Commun., 2008, 18, 113.

    Article  CAS  Google Scholar 

  6. K. Yu. Koltunov, Enantioselektivnyi sintez organicheskikh soedinenii [Enantioselective Synthesis of Organic Compounds], Novosibirsk State Univ., Novosibirsk, 2010, 41 pp. (in Russian).

    Google Scholar 

  7. C. A. Falciola, A. Alexakis, Eur. J. Org. Chem., 2008, 3765.

    Google Scholar 

  8. G. C. Hargaden, P. J. Guiry, Chem. Rev., 2009, 109, 2505.

    Article  CAS  Google Scholar 

  9. A. Börner, in Phosphorus Ligands in Asymmetric Catalysis, Ed. A. Börner, Wiley-VCH, Weinheim, 2008, Vol. 1, p. 28.

  10. M. Diéguez, A. Ruiz, C. Claver, Dalton Trans., 2003, 2957.

    Google Scholar 

  11. A. G. Tolstikov, T. B. Khlebnikova, G. A. Tolstikov, Khimiya i komp’yuternoe modelirovanie. Butlerovskie soobshcheniya [Chemistry and Computor Simulation. Butlerov Communication], 2002, 27 (in Russian).

    Google Scholar 

  12. A. G. Tolstikov, T. B. Khlebnikova, O. V. Tolstikova, G. A. Tolstikova, Russ. Chem. Rev., 2003, 72, 803.

    Article  CAS  Google Scholar 

  13. J. F. Teichert, B. L. Feringa, Angew. Chem., Int. Ed., 2010, 49, 2486.

    Article  CAS  Google Scholar 

  14. Q.-L. Zhou, in Privileged Chiral Ligands and Catalysts, Ed. Q.-L. Zhou, Wiley-VCH, Weinheim, 2011.

  15. J. Ansel, M. Wills, Chem. Soc. Rev., 2002, 31, 259.

    Article  Google Scholar 

  16. A. Alexakis, C. Benhaim, Eur. J. Org. Chem., 2002, 19, 3221.

    Article  Google Scholar 

  17. O. Molt, T. Shrader, Synthesis, 2002, 2633.

    Google Scholar 

  18. K. N. Gavrilov, O. G. Bondarev, A. I. Polosukhin, Russ. Chem. Rev., 2004, 73, 671.

    Article  CAS  Google Scholar 

  19. M. T. Reetz, G. Mehler, A. Meiswinkel, T. Sell, Tetrahedron Lett., 2002, 43, 7941.

    Article  CAS  Google Scholar 

  20. B. H. G. Swennenhuis, R. Chen, P. W. N. M. van Leeuwen, J. G. de Vries, P. C. J. Kamer, Eur. J. Org. Chem., 2009, 5796.

    Google Scholar 

  21. G. Buono, N. Toselli, D. Martin, in Phosphorus Ligands in Asymmetric Catalysis, Ed. A. Börner, Wiley-VCH, Weinheim, 2008, Vol. 2, p. 529.

  22. M. T. Reetz, H. Oka, R. Goddard, Synthesis, 2003, 1809.

    Google Scholar 

  23. J. M. Brunel, T. Constantieux, G. Buono, J. Org. Chem., 1999, 64, 8940.

    Article  CAS  Google Scholar 

  24. G. Delapierre, J. M. Brunel, T. Constantieux, G. Buono, Tetrahedron: Asymmetry, 2001, 12, 1345.

    Article  CAS  Google Scholar 

  25. 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, K. N. Gavrilov, Eur. J. Org. Chem., 2004, 2214.

    Google Scholar 

  26. V. N. Tsarev, S. E. Lyubimov, O. G. Bondarev, A. A. Korlyukov, M. Yu. Antipin, P. V. Petrovskii, V. A. Davankov, A. A. Shiryaev, E. B. Benetsky, P. A. Vologzhanin, K. N. Gavrilov, Eur. J. Org. Chem., 2005, 2097.

    Google Scholar 

  27. K. N. Gavrilov, S. V. Zheglov, M. N. Gavrilova, I. M. Novikov, M. G. Maksimova, N. N. Groshkin, E. A. Rastorguev, V. A. Davankov, Tetrahedron, 2012, 68, 1581.

    Article  CAS  Google Scholar 

  28. M. Kimura, Y. Uozumi, J. Org. Chem., 2007, 72, 707.

    Article  CAS  Google Scholar 

  29. E. B. Benetskiy, C. Bolm, Tetrahedron: Asymmetry, 2011, 22, 373.

    Article  CAS  Google Scholar 

  30. O. G. Bondarev, R. Goddard, Tetrahedron Lett., 2006, 47, 9013.

    Article  CAS  Google Scholar 

  31. R. Mariz, A. Briceno, R. Dorta, Organometallics, 2008, 27, 6605.

    Article  CAS  Google Scholar 

  32. I. S. Mikhel, G. Bernardinelli, A. Alexakis, Inorg. Chim. Acta, 2006, 359, 1826.

    Article  CAS  Google Scholar 

  33. B. Bartets, C. Garcia-Yebra, G. Helmchen, Eur. J. Org. Chem., 2003, 1097.

    Google Scholar 

  34. K. V. L. Crepy, T. Imamoto, Adv. Synth. Catal., 2003, 345, 79.

    Article  CAS  Google Scholar 

  35. Z. Lu, S. Ma, Angew. Chem., Int. Ed., 2008, 47, 258.

    Article  CAS  Google Scholar 

  36. M. Dieguez, O. Pamies, Acc. Chem. Res., 2010, 43, 312.

    Article  CAS  Google Scholar 

  37. H. Fernandez-Perez, P. Etayo, A. Panossian, A. Vidal-Ferran, Chem. Rev., 2011, 111, 2119.

    Article  CAS  Google Scholar 

  38. J. Magano, Tetrahedron, 2011, 67, 7875.

    Article  CAS  Google Scholar 

  39. D. Lafrance, P. Bowles, K. Leeman, R. Rafka, Org. Lett., 2011, 13, 2322.

    Article  CAS  Google Scholar 

  40. B. M. Trost, M. L. Crawley, Chem. Rev., 2003, 103, 2921.

    Article  CAS  Google Scholar 

  41. T. Graening, H.-G. Schmalz, Angew. Chem., Int. Ed., 2003, 42, 2580.

    Article  CAS  Google Scholar 

  42. P. Pelagatti, M. Carcelli, F. Calbiani, C. Cassi, L. Elviri, C. Pelizzi, U. Rizzotti, D. Rogolino, Organometallics, 2005, 24, 5836.

    Article  CAS  Google Scholar 

  43. K. Barta, M. Hölscher, G. Franciò, W. Leitner, Eur. J. Org. Chem., 2009, 4102.

    Google Scholar 

  44. C. A. Tolman, Chem. Rev., 1977, 77, 313.

    Article  CAS  Google Scholar 

  45. A. I. Polosukhin, A. Yu. Kovalevskii, K. N. Gavrilov, Koordinats. Khim., 1999, 25, 812 [Russ. J. Coord. Chem. (Engl. Transl.), 1999, 25, 758].

    Google Scholar 

  46. K. N. Gavrilov, V. N. Tsarev, S. I. Konkin, S. E. Lyubimov, A. A. Korlyukov, M. Yu. Antipin, V. A. Davankov, Eur. J. Inorg. Chem., 2005, 3311.

    Google Scholar 

  47. B. M. Trost, D. L. Van Vranken, C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327.

    Article  CAS  Google Scholar 

  48. S. Carboni, L. Pignataro, C. Gennari, U. Piarulli, Tetrahedron: Asymmetry, 2009, 20, 1185.

    Article  CAS  Google Scholar 

  49. V. Benessere, A. De Roma, R. D. Litto, M. Lega, F. Ruffo, Eur. J. Org. Chem., 2011, 5779.

    Google Scholar 

  50. A. Alexakis, S. Mutti, J. F. Normant, J. Am. Chem. Soc., 1991, 113, 6332.

    Article  CAS  Google Scholar 

  51. K. N. Gavrilov, O. G. Bondarev, R. V. Lebedev, A. A. Shiryaev, S. E. Lyubimov, A. I. Polosukhin, G. V. Grintselev-Knyazev, K. A. Lyssenko, S. K. Moiseev, N. S. Ikonnikov, V. N. Kalinin, V. A. Davankov, A. V. Korostylev, H.-J. Gais, Eur. J. Inorg. Chem., 2002, 1367.

    Google Scholar 

  52. P. R. Auburn, P. B. McKenzie, B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033.

    Article  CAS  Google Scholar 

  53. T. Ukai, H. Kawazura, Y. Ishii, J. Organomet. Chem., 1974, 65, 253.

    Article  CAS  Google Scholar 

  54. K. N. Gavrilov, S. E. Lyubimov, S. V. Zheglov, E. B. Benetsky, V. A. Davankov, J. Mol. Catal. A, 2005, 231, 255.

    Article  CAS  Google Scholar 

  55. D. Seebach, E. Devaquet, A. Emst, M. Hayakawa, F. N. M. Kiihnle, W. B. Schweizer, B. Weher, Helv. Chim. Acta, 1995, 78, 1636.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. A. Esenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    K. N. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, A. A. Shiryaev, O. V. Potapova & I. M. Novikov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    E. A. Rastorguev, P. V. Petrovskii & V. A. Davankov

Authors
  1. K. N. Gavrilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Chuchelkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Zheglov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Shiryaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. V. Potapova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. M. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. A. Rastorguev
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. P. V. Petrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. V. A. Davankov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. N. Gavrilov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1910–1917, October, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gavrilov, K.N., Chuchelkin, I.V., Zheglov, S.V. et al. Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine. Russ Chem Bull 61, 1925–1932 (2012). https://doi.org/10.1007/s11172-012-0267-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-012-0267-3

Key words

Search

Navigation