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Configurationally stable asymmetric nitrogen atom in the palladium(II) aminophosphine complex

  • Organometallic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The synthesis of a new optically active aminophosphine ligandi-Pramphos, containing a potentially stereogenic nitrogen atom, from (S)-N-isopropyl-N-methyl-α-methylbenzylamine is described; its complex with palladium(II) chloride was obtained. NMR spectroscopy revealed that the coordination of the aminophosphine with the metal resulted in stereospecific locking of the donor nitrogen atom in only one of two possible configurations.

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References

  1. K. M. Pietrusiewicz and M. Zablocka,Chem. Rev., 1994,94, 1375.

    Article  CAS  Google Scholar 

  2. K. Burgess, M. J. Ohlmeyer, and K. H. Whitmire,Organometallics, 1992,11, 3588.

    Article  CAS  Google Scholar 

  3. D. G. Allen, S. B. Wild, and D. L. Wood,Organometallics, 1986,5, 1009.

    Article  CAS  Google Scholar 

  4. V. V. Dunina and I. P. Beletskaya,Zh. Org. Khim., 1992,28, 1929 [J. Org. Chem., 1992,28 (Engl. Transl.)].

    CAS  Google Scholar 

  5. V. V. Dunina and I. P. Beletskaya,Zh. Org. Khim., 1992,28, 2368 [J. Org. Chem., 1992,28 (Engl. Transl.)].

    CAS  Google Scholar 

  6. V. V. Dunina and I. P. Beletskaya,Zh. Org. Khim., 1993,29, 806 [J. Org. Chem., 1993,29 (Engl. Transl.)].

    CAS  Google Scholar 

  7. L. Horner and G. Simons,Z. Naturforsch., 1984,39b, 504.

    CAS  Google Scholar 

  8. L. Horner and G. Simons,Z. Naturforsch., 1984,39b, 512.

    CAS  Google Scholar 

  9. R. J. Doyle, G. Salem, and A. C. WillisJ. Chem. Soc., Chem. Commun., 1994, 1587.

  10. C. Bianchini, St. Cicchi, M. Peruzzini, K. M. Pietrusiewicz, and A. Brandi,J. Chem. Soc., Chem. Commun., 1995, 833.

  11. I. Kinoshita, K. Kashiwabara, and J. Fujita,Chem. Lett., 1977, 831.

  12. A. de Renzi, G. Morelli, and M. Scalone,Inorg. Chim. Acta, 1982,65, L119.

    Article  Google Scholar 

  13. H. Brunner and A. F. M. M. Rahman,Chem. Ber., 1984,117, 710.

    CAS  Google Scholar 

  14. J. H. Griffin, and R. M. Kellog,J. Org. Chem., 1985,50, 3261.

    Article  CAS  Google Scholar 

  15. A. Albinati, Fr. Lianza, H. Berger, P. S. Pregosin, H. Ruegger, and R. W. Kunz,Inorg. Chem., 1993,32, 478.

    Article  CAS  Google Scholar 

  16. O. A. Zalevskaya, V. V. Dunina, V. M. Potapov, L. G. Kuz'mina, and Yu. T. Struchkov,Zh. Obshch. Khim., 1985,55, 1332 [J. Gen. Chem., 1985,55 (Engl. Transl.)].

    CAS  Google Scholar 

  17. V. V. Dunina, O. A. Zalevskaya, I. P. Smolyakova, and V. M. Potapov,Zh. Obshch. Khim., 1986,56, 674 [J. Gen. Chem., 1986,56 (Engl. Transl.)].

    CAS  Google Scholar 

  18. L. G. Kuz'mina, Yu. T. Struchkov, V. V. Dunina, O. A. Zalevskaya, and V. M. Potapov,Izv. Akad. Nauk, Ser. Khim., 1986, 1807 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 1639 (Engl. Transl.)].

    Google Scholar 

  19. V. I. Sokolov, L. L. Troitskaya, and T. A. Sorokina,Izv. Akad. Nauk, Ser. Khim., 1971, 2612 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971,20 (Engl. Transl.)].

    Google Scholar 

  20. V. V. Dunina, E. B. Golovan, N. S. Gulyukina, and A. V. Buyevich,Tetrahedron: Asymmetry, 1995,6, 2731.

    Article  CAS  Google Scholar 

  21. L. Horner and G. Simons,Phosphorus and Sulfur, 1983,15, 165.

    CAS  Google Scholar 

  22. J. T. B. H. Jastrzebski and G. van Koten,Inorg. Synthesis, 1989,26, 150.

    CAS  Google Scholar 

  23. G. van Koten and J. T. B. H. Jastrzebski,Tetrahedron, 1989,45, 569.

    Article  Google Scholar 

  24. K. Yamamoto, A. Tomita, and J. Tsuji,Chem. Lett., 1978, 3.

  25. N. C. Payne and D. W. Stephan,Inorg. Chem., 1982,21, 182.

    Article  CAS  Google Scholar 

  26. W. de Graaf, S. Harder, J. Boersma, and G. van Koten,J. Organometal. Chem., 1988,358, 545.

    Article  Google Scholar 

  27. H. -J. Kreuzfeld, Chr. Dobler, H. -P. Abicht,J. Organometal. Chem., 1987,336, 287.

    Article  CAS  Google Scholar 

  28. A. Kinting, H. -J. Kreuzfeld, and H. -P. Abicht,J. Organomet. Chem., 1989,370, 343.

    Article  CAS  Google Scholar 

  29. M. I. Kabachnik, T. Ya. Medved', Yu. M. Polikarpov, and K. S. Yudina,Izv. Akad. Nauk, Ser. Khim., 1961, 2029. [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1961,10 (Engl. Transl.)].

  30. A. C. Cope and T. T. Foster,J. Am. Chem. Soc., 1949,71, 3229.

    Article  Google Scholar 

  31. L. Horner and G. Simons,Phosphorus and Sulfur, 1983,14, 189.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation

    V. V. Dunina, E. B. Golovan, N. S. Gulyukina, Yu. K. Grishin & I. P. Beletskaya

Authors
  1. V. V. Dunina
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  2. E. B. Golovan
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  3. N. S. Gulyukina
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  4. Yu. K. Grishin
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  5. I. P. Beletskaya
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Additional information

The possibility of locking of the configuration of the asymmetric nitrogen atom during cyclopalladation was shown for the first time in Ref. 19 for the prochiral ligand.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1385–1389, July, 1997.

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Dunina, V.V., Golovan, E.B., Gulyukina, N.S. et al. Configurationally stable asymmetric nitrogen atom in the palladium(II) aminophosphine complex. Russ Chem Bull 46, 1331–1334 (1997). https://doi.org/10.1007/BF02495936

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  • DOI: https://doi.org/10.1007/BF02495936

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