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Asymmetric catalysis involving heterocyclic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The newest advances in the realization of asymmetric reactions with the aid of both heterogeneous and metal-complex catalysts are examined. Heterocyclic compounds are used as prochiral substrates and chiral ligands in the compositions of the catalysts. Chief attention is directed to the relationship between the enantioselectivity and the structures of the heterocyclic compounds.

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Literature cited

  1. J. Morrison and H. Mosher, Asymmetric Organic Reactions, American Chemical Society (1976).

  2. I. Izumi and A. Tai, Stereodifferentiating Reactions [Russian translation], Mir, Moscow (1979), p. 116.

    Google Scholar 

  3. E. I. Klabunovskii, Usp. Khim., 51, 1103 (1982).

    Google Scholar 

  4. J. D. Morrison, W. P. Masler, and M. K. Neuberg, Adv. Catal., 25, 81 (1976).

    Google Scholar 

  5. H. B. Kagan, Chem. Commun., No. 8, 401 (1971).

    Google Scholar 

  6. H. B. Kagan and T. P. Dang, J. Am. Chem. Soc., 94, 6429 (1972).

    Google Scholar 

  7. H. B. Kagan, J. Organomet. Chem., 114, 325 (1976).

    Google Scholar 

  8. H. B. Kagan, H. Langlois, and T. P. Dang, Tetrahedron, 32, 233 (1976).

    Google Scholar 

  9. H. B. Kagan, J. Organomet. Chem., 90, 353 (1975).

    Google Scholar 

  10. H. B. Kagan, Pure Appl. Chem., 43, 401 (1975).

    Google Scholar 

  11. R. Glaser and J. Blumenfeld, Tetrahedron Lett., No. 29, 2525, 2527 (1977).

    Google Scholar 

  12. H. B. Kagan, J. Organomet. Chem., 170, 175 (1979).

    Google Scholar 

  13. R. Glaser, S. Geresh, and J. Blumenfeld, J. Organomet. Chem., 112, 355 (1976).

    Google Scholar 

  14. A. P. Stoll and R. Suess, Helv. Chim. Acta, 57, 2487 (1974).

    Google Scholar 

  15. M. Florini, G. M. Giongo, F. Marcati, and W. Marconi, J. Mol. Catal., 1, 451 (1976).

    Google Scholar 

  16. G. Pracejus and H. Pracejus, Tetrahedron Lett., No. 39, 3497 (1977).

    Google Scholar 

  17. V. A. Pavlov and E. N. Rasadkina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1087 (1980).

    Google Scholar 

  18. É. E. Nifant'ev and T. S. Kukhareva, Dokl. Akad. Nauk SSSR, 253, 1584 (1980).

    Google Scholar 

  19. É. E. Nifant'ev (Nifantyev) and S. A. Rumyantseva, Phosphorus Sulfur, 12, 27 (1981).

    Google Scholar 

  20. K. Achiwa, J. Am. Chem. Soc., 98, 8265 (1976).

    Google Scholar 

  21. K. Achiwa, Chem. Lett., No. 7, 777 (1977).

    Google Scholar 

  22. I. Ojima, T. Kogure, and K. Achiwa, Chem. Lett., No. 6, 567 (1978).

    Google Scholar 

  23. I. Ojima, T. Kogure, and T. Terasaki, J. Org. Chem., 43, 3444 (1978).

    Google Scholar 

  24. E. I. Karpeiskaya, L. F. Godunova, E. S. Neupokoeva, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1443 (1974).

    Google Scholar 

  25. P. H. Boyle and M. I. Keating, Chem. Commun., No. 10, 375 (1974).

    Google Scholar 

  26. Y. Ohgo, Preprints from the 5th Research Conference on Catalysis, Osaka (1975), p. 12.

  27. R. W. Waldron and J. H. Weber, Inorg. Chem., 16, 1220 (1977).

    Google Scholar 

  28. Y. Ohashi, Y. Sasada, and Y. Tashiro, Bull. Chem. Soc. Jpn., 46, 2589 (1973).

    Google Scholar 

  29. E. I. Klabunovskii and A. A. Vedenyapin, Asymmetric Catalysis. Hydrogenation on Metals [in Russian], Nauka, Moscow (1980), p. 59.

    Google Scholar 

  30. M. E. Wilson and G. M. Whitesides, J. Am. Chem. Soc., 100, 306 (1978).

    Google Scholar 

  31. D. Lipkin and T. D. Stewart, J. Am. Chem. Soc., 61, 3295, 3297 (1939).

    Google Scholar 

  32. T. Isoda, I. Ichikawa, and T. Shimamoto, J. Sci. Res. Inst., 34, 134 (1958).

    Google Scholar 

  33. Y. Izumi, M. Imaida, H. Fukawa, and S. Akabori, Bull. Chem. Soc. Jpn., 36, 21 (1963).

    Google Scholar 

  34. T. Isoda, I. Ichikawa, and T. Shimamoto, J. Sci. Res. Inst., 34, 143 (1958).

    Google Scholar 

  35. S. Senoh, S. Ouichi, and K. Tsunoda, Japanese Patent No. 3307; Chem. Abstr., 60, 3092 (1974).

    Google Scholar 

  36. E. I. Klabunovskii, A. A. Vedenyapin, and E. I. Karpeiskaya, Preprints from the 5th Research Conference on Catalysis, Osaka (1975), p. 15.

  37. E. I. Karpeiskaya, E. S. Neupokoeva, L. F. Godunova, and E. I. Klabunovskii, Preprints of the 6th International Congress on Heterocyclic Chemistry, Teheran (1977), p. 429.

  38. E. I. Klabunovskii, A. A. Vedenyapin, E. I. Karpeiskaya, and V. A. Pavlov, in: Proceedings of the 7th International Congress on Catalysis, Tokyo (1980), Kodansha (1981), p. 390.

  39. E. I. Karpeiskaya, L. F. Godunova, E. S. Neupokoeva, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 139, 146 (1979).

    Google Scholar 

  40. L. F. Godunova, E. I. Karpeiskaya, E. S. Neupokoeva, and E. I. Klabunovskii, in: Catalytic Reactions in the Liquid Phase [in Russian], Nauka, Alma Ata (1974), p. 121.

    Google Scholar 

  41. E. I. Karpeiskaya, L. F. Godunova, E. S. Neupokoeva, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1104 (1978); No. 6, 1363, 1368.

    Google Scholar 

  42. E. S. Levitina, E. I. Karpeiskaya, L. F. Godunova, and E. I. Klabunovskii, in: News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 1, Zinatne, Riga (1979), p. 175.

    Google Scholar 

  43. Y. Izumi, Angew. Chem., Int. Ed., 10, 871 (1971).

    Google Scholar 

  44. Ya. D. Fridman and E. I. Klabunovskii, Kinet. Katal., 21, 1199 (1980).

    Google Scholar 

  45. Y. Izumi, H. Takizawa, and K. Nakagawa, Bull. Chem. Soc. Jpn., 43, 1792 (1970).

    Google Scholar 

  46. E. N. Lipgart, Yu. I. Petrov, and E. I. Klabunovskii, Kinet. Katal., 12, 1491 (1971).

    Google Scholar 

  47. E. I. Klabunovskii, Zh. Fiz. Khim., 47, 1353 (1973).

    Google Scholar 

  48. M. J. Fish and D. F. Ollis, J. Catal., 50, 353 (1977).

    Google Scholar 

  49. M. J. Fish and D. F. Ollis, Catal. Rev., 18, 259 (1978).

    Google Scholar 

  50. I. Yasumori, Pure Appl. Chem., 50, 971 (1978).

    Google Scholar 

  51. Y. Orito, S. Imai, S. Niwa, and N. G. Hung, J. Synth. Org. Chem. Jpn., 37, 173 (1979).

    Google Scholar 

  52. Y. Orito, S. Imai, and S. Niwa, J. Chem. Soc. Jpn. (Chem. Ind. Chem.) [Nippon Kagaku Kaishi], 83, 670 (1980).

    Google Scholar 

  53. E. I. Klabunovskii, Stereospecific Catalysis [in Russian], Nauka, Moscow (1968), p. 223.

    Google Scholar 

  54. G. Henrici-Olive and S. Olive, Coordination and Catalysis, Verlag Chemie (1977).

  55. G. Consiglio, C. Batteghi, C. Salomon, and P. Pino, Angew. Chem., Int. Ed., 12, 669 (1973).

    Google Scholar 

  56. G. Consiglio and P. Pino, Helv. Chim. Acta, 59, 642 (1976).

    Google Scholar 

  57. J. M. Brown and P. A. Choloner, J. Am. Chem. Soc., 100, 4307 (1978).

    Google Scholar 

  58. C. Batteghi, G. Consiglio, and P. Pino, Chimia, 27, 477 (1973).

    Google Scholar 

  59. T. Ogata, T. Masomo, I. Yoshikazu, and H. Taruyuki, Japanese Patent No. 5257108; Ref. Zh. Khim., 2N132P (1978).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

    E. I. Klabunovskii

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  1. E. I. Klabunovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 291–303, March, 1983.

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Klabunovskii, E.I. Asymmetric catalysis involving heterocyclic compounds (review). Chem Heterocycl Compd 19, 233–243 (1983). https://doi.org/10.1007/BF00513251

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  • DOI: https://doi.org/10.1007/BF00513251

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