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From transition metals to organocatalysis

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Abstract

Several classes of transition metal-catalyzed reactions and the gradual transition to organocatalysis are summarized as the authors’ personal account. This includes a brief overview of novel nonsymmetrically substituted 1,1′-binaphthyls and their application in Pd-catalyzed reactions and as chiral phase-transfer catalysts, and new chiral complexes of 2,2′-bipyridine-type ligands with Mo, Cu, and Pd and their catalytic applications. The attention is focused on chiral pyridine-type N-oxides as novel Lewis-basic organocatalysts applied in allylation of aromatic aldehydes with allyltrichlorosilane.

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References

  1. P. Kocovsky, Collect. Czech. Chem. Commun., 1994, 59, 1; (b) P. Kocovsky, A. Malkov, S. Vyskocil, and G. C. Lloyd-Jones, Pure Appl. Chem., 1999, 71, 1425; (c) P. Kocovsky, J. Organomet. Chem., 2003, 687, 256.

    Article  CAS  Google Scholar 

  2. P. Kocovsky, S. Vyskocil, and M. Smrcina, Chem. Rev., 2003, 103, 3213.

    Article  CAS  PubMed  Google Scholar 

  3. M. Smrcina, M. Lorenc, V. Hanus, and Kocovsky, Synlett, 1991, 231; (b) M. Smrcina, M. Lorenc, V. Hanus, P. Sedmera, and P. Kocovsky, J. Org. Chem., 1992, 57, 1917; (c) M. Smrcina, J. Polakova, S. Vyskocil, and P. Kocovsky, J. Org. Chem., 1993, 58, 4534; (d) M. Smrcina, S. Vyskocil, B. Maca, M. Polasek, T. A. Claxton, and A. P. Abbott, J. Org. Chem., 1994, 59, 2156; (e) M. Smrcina, S. Vyskocil, J. Polivkova, J. Polakova, and P. Kocovsky, Collect. Czech. Chem. Commun., 1996, 61, 1520; (f) S. Vyskocil, M. Smrcina, M. Lorenc, V. Hanus, M. Polasek, and P. Kocovsky, Chem. Commun., 1998, 585; (g) S. Vyskocil, M. Smrcina, M. Lorenc, I. Tislerova, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, and P. Kocovsky, J. Org. Chem., 2001, 66, 1359; (h) K. Ding, Y. Wang, H. Yun, J. Liu, Y. Wu, M. Terada, Y. Okubo, and K. Mikami, Chem. Eur. J., 1999, 5, 1734; (i) K. Korber, W. Tang, X. Hu, and X. Zhang, Tetrahedron Lett., 2002, 43, 7163.

  4. S. Vyskocil, L. Meca, I. Tislerova, I. Cisarova, M. Polasek, S. R. Harutyunyan, Y. N. Belokon, R. M. J. Stead, L. Farrugia, and P. Kocovsky, Chem. Eur. J., 2002, 8, 4633.

    Article  CAS  Google Scholar 

  5. M. Smrcina, J. Polivkova, S. Vyskocil, J. Polakova, J. Sejbal, V. Hanus, M. Polasek, H. Verrier, and P. Kocovsky, Tetrahedron: Asymmetry, 1997, 8, 537.

    Article  CAS  Google Scholar 

  6. S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, and P. Kocovsky, J. Org. Chem., 1998, 63, 7738.

    Article  CAS  Google Scholar 

  7. S. Vyskocil, S. Jaracz, M. Smrcina, M. Sticha, V. Hanus, M. Polasek, and P. Kocovsky, J. Org. Chem., 1998, 63, 7727.

    Article  CAS  Google Scholar 

  8. Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, S. Vyskocil, and H. B. Kagan, Tetrahedron: Asymmetry, 1999, 10, 1723; (b) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, S. Vyskocil, and H. B. Kagan, J. Org. Chem., 2000, 65, 7041; (c) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutyunyan, S. Vyskocil, M. North, and H. B. Kagan, Angew. Chem., Int. Ed., 2001, 40, 1948.

    Article  CAS  Google Scholar 

  9. Y. N. Belokon, N. B. Bespalova, T. D. Churkina, I. Cisarova, M. G. Ezernitskaya, S. R. Harutyunyan, H. B. Kagan, P. Kocovsky, K. A. Kochetkov, O. V. Larionov, K. A. Lyssenko, M. North, A. S. Peregudov, V. V. Prisyazhnyuk, and S. Vyskocil, J. Am. Chem. Soc., 2003, 125, 12860.

    Article  CAS  PubMed  Google Scholar 

  10. E. M. Carreira, R. A. Singer, and W. Lee, J. Am. Chem. Soc., 1994, 116, 8837; (b) E. M. Carreira, W. Lee, and R. A. Singer, J. Am. Chem. Soc., 1995, 117, 3649; (c) R. A. Singer and E. M. Carreira, J. Am. Chem. Soc., 1995, 117, 12360; (d) R. A. Singer, M. S. Shepard, and E. M. Carreira, Tetrahedron, 1998, 54, 7025.

    Article  CAS  Google Scholar 

  11. W. Tang, X. Hu, and X. Zhang, Tetrahedron Lett., 2002, 43, 3075.

    Article  CAS  Google Scholar 

  12. H. Brunner, F. Henning, and M. Weber, Tetrahedron: Asymmetry, 2002, 13, 37.

    Article  CAS  Google Scholar 

  13. Y. Yuan, J. Long, J. Sun, and K. Ding, Chem. Eur. J., 2002, 8, 5033.

    Article  CAS  Google Scholar 

  14. J. J. Van Veldhuizen, S. B. Garber, J. S. Kingsbury, and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 4954.

    Article  PubMed  Google Scholar 

  15. J. J. Van Veldhuizen, D. G. Gillingham, S. B. Garber, O. Kataoka, and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 12502.

    Article  PubMed  Google Scholar 

  16. A. Ford and S. Woodward, Angew. Chem., Int. Ed., 1999, 38, 335; (b) A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, and S. Woodward, Chem. Eur. J., 2000, 6, 3586.

    Google Scholar 

  17. P. Kocovsky, S. Vyskocil, I. Cisarova, J. Sejbal, I. Tislerova, M. Smrcina, G. C. Lloyd Jones, S. C. Stephen, C. P. Butts, M. Murray, and V. Langer, J. Am. Chem. Soc., 1999, 121, 7714; (b) G. C. Lloyd-Jones, S. C. Stephen, M. Murray, C. P. Butts, S. Vyskocil, and P. Kocovsky, Chem. Eur. J., 2000, 6, 4348; (c) I. J. S. Fairlamb, G. C. Lloyd-Jones, S. Vyskocil, and P. Kocovsky, Chem. Eur. J., 2002, 8, 4443; (d) L. Gouriou, G. C. Lloyd-Jones, S. Vyskocil, and P. Kocovsky, J. Organomet. Chem., 2003, 687, 525.

    Article  CAS  Google Scholar 

  18. S. Vyskocil, M. Smrcina, and P. Kocovsky, Tetrahedron Lett., 1998, 39, 9289.

    Article  CAS  Google Scholar 

  19. J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2000, 122, 12051; (b) J. Yin, M. P. Rainka, X.-X. Zhang, and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 1162.

    Article  CAS  Google Scholar 

  20. A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadigishi, and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 4369; (b) J. Ahman, J. P. Wolfe, M. V. Troutman, M. Palucki, and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 1918; (c) J. M. Fox, X. Huang, A. Chieffi, and S. L. Buchwald, J. Am. Chem. Soc., 2000, 122, 1360; (d) D. W. Old, J. P. Wolfe, and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 9722; (e) D. W. Old, M. C. Harris, and S. L. Buchwald, Org. Lett., 2000, 2, 1403; (f) K. E. Torraca, S. Kuwabe, and S. L. Buchwald, J. Am. Chem. Soc., 2000, 122, 12907; (g) A. Chieffi, K. Kamikawa, J. Ahman, J. M. Fox, and S. L. Buchwald, Org. Lett., 2001, 3, 1897; (h) W. A. Morandi and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7996; (i) K. E. Torraca, X. Huang, C. A. Parrish, and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 10770; (j) S. Kuwabe, K. E. Torraca, and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 12202; (k) T. Hamada and S. L. Buchwald, Org. Lett., 2002, 4, 999; (l) J. Yin, M. P. Rainka, X.-X. Zhang, and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 1162; (m) M. C. Harris, X. Huang, and S. L. Buchwald, Org. Lett., 2002, 4, 2885.

    Article  CAS  Google Scholar 

  21. X. Hu, H. Chen, and X. Zhang, Angew. Chem., Int. Ed., 1999, 38, 3518.

    Google Scholar 

  22. A. V. Malkov, M. Bella, V. Langer, and P. Kocovsky, Org. Lett., 2000, 2, 3047; (b) A. V. Malkov, I. R. Baxendale, J. Fawcett, D. R. Russel, V. Langer, D. J. Mansfield, M. Valko, and P. Kocovsky, Organometallics, 2001, 20, 673.

    Article  CAS  PubMed  Google Scholar 

  23. A. V. Malkov, D. Pernazza, M. Bell, M. Bella, A. Massa, F. Teply, P. Meghani, and P. Kocovsky, J. Org. Chem., 2003, 68, 4727.

    Article  CAS  PubMed  Google Scholar 

  24. A. V. Malkov, M. Bella, I. G. Stara, and P. Kocovsky, Tetrahedron Lett., 2001, 42, 3045.

    Article  CAS  Google Scholar 

  25. A. V. Malkov and P. Kocovsky, Curr. Org. Chem., 2003, 7, 1737; (b) G. Chelucci and R. P. Thummel, Chem. Rev., 2002, 102, 3129; (c) N. C. Fletcher, J. Chem. Soc., Perkin Trans. 1, 2002, 1831; (d) G. Chelucci, G. Murineddu, G. A. Pinna, Tetrahedron: Asymmetry, 2004, 15, 1373.

    Article  CAS  Google Scholar 

  26. U. Knof and A. von Zelewsky, Angew. Chem., Int. Ed., 1999, 38, 303; (b) D. Lotscher, S. Rupprecht, H. Stoeckli-Evans, and A. von Zelewsky, Tetrahedron: Asymmetry, 2000, 11, 4341; (c) B. Kolp, D. Abeln, H. Stoeckli-Evans, and A. von Zelewsky, Eur. J. Inorg. Chem., 2001, 1207; (d) S. Lotscher, S. Rupprecht, P. Collomb, P. Belser, H. Viebrock, A. von Zelewsky, and P. Burger, Inorg. Chem., 2001, 40, 5675.

    Google Scholar 

  27. G. Chelucci, A. Saba, and F. Soccolini, Tetrahedron Lett., 2001, 57, 9989.

    CAS  Google Scholar 

  28. M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto, J. Am. Chem. Soc., 1998, 120, 6419.

    Article  CAS  Google Scholar 

  29. A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, and P. Kocovsky, Org. Lett., 2002, 4, 1047; (b) A. V. Malkov, M. Bell, M. Orsini, D. Pernazza, A. Massa, P. Herrmann, P. Meghani, and P. Kocovsky, J. Org. Chem., 2003, 68, 9659.

    Article  CAS  PubMed  Google Scholar 

  30. T. Shimada, A. Kina, S. Ikeda, and T. Hayashi, Org. Lett., 2002, 4, 2799; (b) T. Shimada, A. Kina, and T. Hayashi, J. Org. Chem., 2003, 68, 6329.

    Article  CAS  PubMed  Google Scholar 

  31. A. V. Malkov, M. Bell, M. Vassieu, V. Bugatti, and P. Kocovsky, J. Mol. Catal. A, 2003, 196, 179.

    Article  CAS  Google Scholar 

  32. C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5525; (b) M. S. Cubberley and B. L. Iverson, J. Am. Chem. Soc., 2001, 123, 7560; (c) G. A. Breault, C. A. Hunter, and P. C. Mayers, J. Am. Chem. Soc., 1998, 120, 3402; (d) F. J. Carver, C. A. Hunter, D. J. Livingstone, J. F. McCabe, and E. M. Seward, Chem. Eur. J., 2002, 8, 2848; (e) M. O. Sinnokrot and C. D. Sherrill, J. Am. Chem. Soc., 2004, 126, 7690.

    Article  Google Scholar 

  33. A. V. Malkov, L. Dufkova, L. Farrugia, and P. Kocovsky, Angew. Chem., Int. Ed., 2003, 42, 3674.

    Google Scholar 

  34. A. V. Malkov, A. Mariani, K. N. MacDougall, and P. Kocovsky, Org. Lett., 2004, 6, 2253.

    Article  CAS  PubMed  Google Scholar 

  35. G. C. Lloyd-Jones, Synlett, 2001, 161.

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Dedicated to Prof. Belokon’ in appreciation of his achivements in asymmetric catalysis.

Based on the report presented by P. Kocovsky at the International Conference “Modern Trends in Organoelement and Polymer Chemistry” dedicated to the 50th anniversary of the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences (Moscow, May 30–June 4, 2004).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1733–1738, September, 2004.

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Kocovsky, P., Malkov, A.V. From transition metals to organocatalysis. Russ Chem Bull 53, 1806–1812 (2004). https://doi.org/10.1007/s11172-005-0040-y

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  • DOI: https://doi.org/10.1007/s11172-005-0040-y

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