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Chiral 4-piperidones and their bicyclic analogs. Strategy of stereoselective synthesis (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The principal stereoselective paths of synthesis and the stereochemistry of chiral 4 piperidones and their bicyclic analogs are examined critically in this article.

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References

  1. G. M. Whitesides and D. W. Lewis, J. Am. Chem. Soc.,92, 6979 (1970).

    Google Scholar 

  2. The Merck Index, 11th Ed., Merck & Co., Rahway, N.J. (1989).

  3. C. R. Ganeilin and R. G. Spickett, J. Med. Chem.,8, 619 (1965).

    PubMed  Google Scholar 

  4. A. A. Champseix and G. R. Lefur, Eur. Pat. 12,643; Chem. Abstr.,94, 15175 (1981).

    Google Scholar 

  5. S. Samczuk and H. K. F. Hermans, Ger. Pat. 2,642,856; Chem. Abstr.,87, 53094 (1977).

    Google Scholar 

  6. Ciba-Geigy, Fr. Pat. 2,437,405; Chem. Abstr., 94, 83739 (1981).

  7. E. Abignente and M. Biniecka-Picazio, Acta. Pol. Pharm.,34, 241 (1977).

    PubMed  Google Scholar 

  8. M. Nalanishi, M. Shiraki, T. Kobayakawa, and R. Kobayashi, Jpn. Pat. 74-03987; Chem. Abstr.,81, 120485 (1974).

    Google Scholar 

  9. I. N. Nazarov, N. S. Prostakov, N. A. Mikheeva, and V. N. Dobrynina, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol.,2, 726 (1959).

    Google Scholar 

  10. P. S. Portoghese, J. Pharm. Sci.,55, 865 (1966).

    PubMed  Google Scholar 

  11. A. Ziering and I. Lee, J. Org. Chem.,12, 911 (1947).

    Google Scholar 

  12. I. Lee, A. Ziering, S. D. Heinemann, and L. Berger, J. Org. Chem.,12, 885 (1947).

    Google Scholar 

  13. A. Ziering, S. D. Heinemann, and I. Lee, J. Org. Chem.,12, 894 (1947).

    Google Scholar 

  14. L. Berger, A. Ziering, and I. Lee, J. Org. Chem.,12, 904 (1947).

    Google Scholar 

  15. I. N. Nazarov, Selected Works [in Russian], Izd. Akad. Nauk SSSR, Moscow (1961), p. 588.

    Google Scholar 

  16. N. S. Prostakov and L. A. Gaivoronskaya, Usp. Khim.,47, 859 (1978).

    Google Scholar 

  17. D. L. Larson and P. S. Portoghese, J. Med. Chem.,16, 195 (1973).

    PubMed  Google Scholar 

  18. D. S. Fries and P. S. Portoghese, J. Med. Chem.,17, 990 (1974).

    PubMed  Google Scholar 

  19. D. S. Fries and P. S. Pomoghese, J. Med. Chem.,19, 1155 (1976).

    PubMed  Google Scholar 

  20. D. S. Fries, R. D. Dodge, H. Hope, and P. S. Portoghese, J. Med. Chem.,25, 9 (1982).

    PubMed  Google Scholar 

  21. P. S. Portoghese, Z. S. D. Gomaa, and D. L. Larson, J. Med. Chem.,16, 199 (1973).

    PubMed  Google Scholar 

  22. K. H. Bell and P. S. Portoghese, J. Med. Chem.,17, 129 (1974).

    PubMed  Google Scholar 

  23. M. Froimowitz, J. Med. Chem.,25, 1127 (1982).

    PubMed  Google Scholar 

  24. C. J. Barnett, C. R. Copley-Merriman, and J. Maki, J. Org. Chem.,54, 4795 (1989).

    Google Scholar 

  25. D. M. Zimmerman, U.S. Pat. 4,081,450; Chem. Abstr.,89, 109113 (1978).

    Google Scholar 

  26. D. M. Zimmerman, R. Nickander, J. S. Horng, and D. T. Wong, Nature,275, 332 (1978).

    PubMed  Google Scholar 

  27. A. Jonczyk, M. Jawdosiuk, M. Makosza, and J. Czyzewski, Przem. Chem.,57, 131 (1978).

    Google Scholar 

  28. N. Lalinde, J. Moliterni, D. Wright, H. K. Spenatr, M. N. Ossipov, T. C. Spaulding, and F. G. Rudo, J. Med. Chem,33, 2876 (1990).

    PubMed  Google Scholar 

  29. J. L. Archibald, Br. Pat. 1,411,783; Chem. Abstr.,84, 43876 (1976).

    Google Scholar 

  30. T. N. Riley, D. S. Hale, and M. C. Wilson, J. Pharm. Sci.,62, 983 (1973).

    PubMed  Google Scholar 

  31. W. F. M. van Bever, C. J. E. Niemegeers, and P. A. J. Janssen, J. Med. Chem.,17, 1047 (1974).

    PubMed  Google Scholar 

  32. M. Nogradi, Stereoselective Synthesis, VCH Publications, New York (1986).

    Google Scholar 

  33. E. A. Mystryukov and G. N. Smirnova, Tetrahedron,27, 375 (1971).

    Google Scholar 

  34. P. Geneste, J. Hugon, C. Reminiac, G. Lamaty, and J. P. Roque, Bull. Soc. Chlm. Fr., No. 5–6, 845 (1976).

  35. R. E. Lyle and G. G. Lyle, J. Org. Chem.,24, 1679 (1959).

    Google Scholar 

  36. É. A. Mlstryukov, N. I. Aranova, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 932 (1961).

  37. G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, T. A. Gudasheva, I. F. Leshcheva, N. M. Sergeev, T. A. Kudryavtseva, and E. Yu. Korchagina, Khim. Geterotsikl. Soedin., No. 12, 1693 (1983).

  38. G. V. Grishina, V. M. Potapov, T. A. Gudasheva, and S. A. Abdulganeeva, Khim. Geterotsikl. Soedin., No. 10, 1378 (1985).

  39. G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, and E. Yu. Korchagina, Khim. Geterotsikl. Soedin., No. 12, 1648 (1985).

  40. G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, T. A. Gudasheva, A. A. Karapetyan, and A. A. Espenbetov, Khim. Geterotsikl. Soedin., No. 12, 1641 (1986).

  41. I. F. Leshcheva, N. M. Sergeev, G. V. Grishina, and V. M. Potapov, Khim. Geterotsiki. Soedin., No. 11, 1503 (1986).

  42. A. É. A1iev, A. A. Fomichev, G. V. Grishina, Yu. I. Él'natanov, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1760 (1990).

  43. S.-I. Yamada, K. Hiroi, and K. Achiwa, Tetrahedron Lett., No. 48, 4233 (1969).

  44. K. Hiroi, K. Achlwa, and S.-I. Yamada, Chem. Bull. Pharm.,20, 246 (1972).

    Google Scholar 

  45. J. K. Whitesell and S. W. Feiman, J. Org. Chem.,42, 1663 (1977).

    Google Scholar 

  46. S. J. Blarer, W. B. Schweizer, and D. Seebach, Helv. Chim. Acta,65, 1637 (1982).

    Google Scholar 

  47. C. Stetin, B. DeJeso, and J.-C. Pommier, J. Org. Chem.,50, 3863 (1985).

    Google Scholar 

  48. A. I. Meyers, D. R. Williams, and M. Druelinger, J. Am. Chem. Soc.,98, 3032 (1976).

    Google Scholar 

  49. J. K. Whltesell and M. A. Whitesell, J. Org. Chem.,42, 377 (1977).

    Google Scholar 

  50. D. I. Hashimoto and K. Koga, Tetrahedron Lett., No. 6, 573 (1978).

  51. A. I. Meyers, D. R. Williams, G. W. Erickson, S. White, and M. Druelinger, J. Am. Chem. Soc.,103, 3081 (1981).

    Google Scholar 

  52. G. V. Grishina, V. M. Potapov, and S. A. Abdulganeeva, Vestn. Mosk. Gos. Univ., Khim.,24, 507 (1983).

    Google Scholar 

  53. G. V. Grishina, V. M. Potapov, and S. A. Abdulganeeva, Khim. Geterotsikl. Soedin., No. 3, 372 (1986).

  54. G. V. Grlshina, V. M. Potapov, S. A. Abdulganeeva, and I. A. Ivanova, Khim. Geterotsikl. Soedin., No. 11, 1510 (1983).

  55. G. V. Grishina, S. A. Abdulganeeva, V. M. Potapov, I. A. Ivanova, A. A. Espenbetov, Yu. T. Struchkov, I. A. Grishina, and A. I. Dutsenko, Khim. Geterotsikl. Soedin., No. 12, 1656 (1985).

  56. V. Schilay, A. Alyev, and G. Grishina, Bull. Soc. Chem. Belg., No. 8, 742 (1992).

  57. G. V. Grishina and E. L. Gaidarova, Khim. Geterotsikl. Soedin., No. 8, 1072 (1992).

  58. E. L. Gaidarova and G. V. Grishina, Synlett., No. 1, 89 (1992).

  59. J. d'Angelo, D. Desmaele, F. Dumas, and A. Guingant, Tetrahedron: Asymmetry,3, 459 (1992).

    Google Scholar 

  60. G. V. Grishina, E. L. Gaidarova, and A. É. Aliev, Khim. Geterotsikl. Soedin., No. 10, 1369 (1992).

  61. V. M. Potapov, G. V. Kiryushkina (Grishina), and G. P. Tokmakov, Khim. Geterotsikl. Soedin., No. 12, 1656 (1972).

  62. V. M. Potapov, G. V. Grishina, E. A. Golov, P. B. Terent'ev, and R. Khertsshu, Khim. Geterotsikl. Soedin., No. 7, 953 (1976).

  63. V. M. Potapov, G. V. Grishina, and E. A. Golov, Khim. Geterotsikl. Soedin., No. 8, 1093 (1976).

  64. I. F. Leshcheva, N. M. Sergeev, G. V. Grishina, and V. M. Potapov, Khim. Geterotsikl. Soedin., No. 2, 230 (1983).

  65. A. É. Aliev and G. V. Grishina, Khim. Geterotsikl. Soedin., No. 2, 271 (1989).

  66. W. L. F. Armarego, in: Stereochemistry of Heterocyclic Compounds, Part I, Nitrogen Heterocycles, Wiley Interscience (1977), p. 141.

  67. G. V. Grishina and V. M. Potapov, Khim. Geterotsikl. Soedin., No. 5, 579 (1987).

  68. G. V. Grishina, N. E. Agafonov, and V. M. Potapov, Khim. Geterotsikl. Soedin., No. 4, 519 (1983).

  69. G. V. Grishina, G. N. Koval', and V. M. Potapov, Khim. Geterotsikl. Soedin., No. 9, 1230 (1978).

  70. V. M. Potapov, G. V. Grishina, and G. N. Koval', Khim. Geterotsikl. Soedin., No. 4, 508 (1978).

  71. V. M. Potapov, G. V. Grishina, E. V. Korotkov, and G. N. Koval', Khim. Geterotsikl. Soedin., No. 4, 511 (1976).

  72. L. A. Kutulya, T. V. Khandrimailova, G. V. Grishina, G. M. Makeev, and M. Yu. Kornilov, Zh. Org. Khim.,27, 2165 (1991).

    Google Scholar 

  73. V. M. Potapov, G. V. Grishina, and G. N. Koval', Khim. Geterotsikl. Soedin., No. 9, 1286 (1976).

  74. V. M. Potapov, G. V. Grishina, and T. A. Liberchuk, Khim. Geterotsikl. Soedin., No. 2, 240 (1978).

  75. V. M. Potapov, G. V. Grishina, and T. A. Gudasheva, Khim. Geterotsikl. Soedin., No. 1, 101 (1980).

  76. G. V. Grishina, V. M. Potapov, and T. V. Tyrtysh, Khim. Geterotsikl. Soedin., No. 3, 389 (l984).

  77. I. N. Azerbaev, K. B. Erzhanov, T. S. Sadykov, N. P. Polatbekov, and V. P. Reshetov, Material from International Symposium of CMEA Member Countries [in Russian], Rushchino (1975), Part 1, p. 148.

  78. S. A. Abdulganeeva, G. V. Grishina, V. M. Potapov, K. B. Erzhanov, and A. A. Shapovalov, Khim. Geterotsikl. Soedin., No. 4, 501 (1983).

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M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, Nos. 11–12, pp. 1619–1648, November–December, 1994. Original article submitted November 11, 1994.

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Grishina, G.V., Gaidarova, E.L. & Zefirov, N.S. Chiral 4-piperidones and their bicyclic analogs. Strategy of stereoselective synthesis (review). Chem Heterocycl Compd 30, 1401–1426 (1994). https://doi.org/10.1007/BF01172866

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