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Synthesis and stereochemistry of chiral 2-azetidinones and 2-azetidinethiones. 2.* Study of the chiroptical properties of some 2-azetidinones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Circular dichroism (CD) spectra were taken for 13 2-azetidinones with one, two, and three asymmetric sites. A possible correlation was found between the sign of the Cotton effect (CE) of the n-π* transition of the amide chromophore with the absolute configuration of the endocyclic stereocenters of 3-methyl-, 4-methyl-, and 3,4-dimethyl-2-azetidinones both with and without an achiral N-α, α-dimethylbenzyl or chiral N-α-methylbenzyl substituent.

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References

  1. N. N. Romanova, T. G. Tallo, and Yu. G. Bundel', in print (1995).

  2. H. Rehling and H. Jensen, Tetrahedron Lett., No. 27, 2793 (1972).

  3. J. Hauer and J. Sebenda, Coll. Czech. Chem. Commun.,48, 1597 (1983).

    Google Scholar 

  4. T. Polonski and M. J. Milewska, Croat. Chem. Acta,62(2A), 129 (1989).

    Google Scholar 

  5. N. D. Berova, S. C. Christoskova, E. M. Simova, and B. J. Kurtev, Comp. Rend. Acad. Bulg. Sci.,35, 657 (1982).

    Google Scholar 

  6. R. Busson and H. Vanderhaeghe, J. Org. Chem.,43, 4438 (1978).

    Google Scholar 

  7. D. B. Boyd, J. P. Riehl, and F. S. Richardson, Tetrahedron,35, 1499 (1979).

    Google Scholar 

  8. R. Busson, E. Roets, and H. Vanderhaeghe, J. Org. Chem.,43, 4434 (1978).

    Google Scholar 

  9. S. Harada, S. Tsubotani, S. Shinagawa, and M. Asai, Tetrahedron,39, 75 (1983).

    Google Scholar 

  10. N. N. Romanova, V. A. Budylin, G. V. Grishina, V. M. Potapov, V. N. Torocheshnikov, M. L. Demchuk, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 12, 1644 (1984).

  11. N. N. Romanova, V. A. Budylin, G. V. Grishina, V. M. Potapov, M. L. Demchuk, I. Yu. Sivkova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 5, 607 (1986).

  12. N. N. Romanova, T. G. Tallo, A. A. Borisenko, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 7, 914 (1990).

  13. N. N. Romanova, V. A. Budylin, G. V. Grishina, V. M. Potapov, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 1, 134 (1985).

  14. H. Bestian and H. Jensen, Patent No. 1,897,498 Ger. Offen; Chem. Abstr.73, 45312 (1970).

    Google Scholar 

  15. K.-D. Kampe, Patent No. 1,807,496 Ger. Offen,73, 45313 (1970).

  16. K. Okano, T. Morimoto, and M. Sekiya. J. Chem. Soc., Chem. Commun., No. 13, 883 (1984).

  17. S. Okamoto, T. Harada, and A. Tai, Bull. Chem. Soc. Jpn.,52, 2670 (1979).

    Google Scholar 

  18. J. A. Schellman and P. Oriel, J. Chem. Phys.,37, 2114 (1962).

    Google Scholar 

  19. B. J. Litman and J. A. Schellman, J. Phys. Chem.,69, 978 (1965).

    Google Scholar 

  20. J. A. Schellman and E. B. Nielson, J. Phys. Chem.,71, 3914 (1967).

    Google Scholar 

  21. F. S. Richardson, R. Strickland, and D. D. Shillady, J. Phys. Chem.,77, 248 (1973).

    Google Scholar 

  22. R. E. Geiger and G. H. Wagniere, Helv. Chem. Acta,58, 738 (1975).

    Google Scholar 

  23. W. Klyne, D. N. Kirk, J. Tilley, and H. Suginome, Tetrahedron,36, 543 (1980).

    Google Scholar 

  24. E. C. Ong, L. C. Cusachs, and O. E. Weigang, J. Chem. Phys.,67, 3289 (1977).

    Google Scholar 

  25. D. W. Urry, J. Phys. Chem.,72, 3035 (1968).

    Google Scholar 

  26. K. Blaha, P. Malon, M. Tichy, I. Fric, R. Usha, S. Ramakumar, and K. Venkatesan, Coll. Czech. Chem. Commun.,43, 3241 (1978).

    Google Scholar 

  27. N. J. Greenfield and G. D. Fasman, J. Am. Chem. Soc.,92, 177 (1970).

    Google Scholar 

  28. E. F. Paulus, D. Kobelt, and H. Jensen, Angew. Chem.,81, 1048 (1969).

    Google Scholar 

  29. J. Luche, H. B. Kagan, R. Parthasarathy, G. Tsoucaris, C. de Rango, and C. Zehwer, Tetrahedron,24, 1275 (1968).

    Google Scholar 

  30. L. M. Jackman, R. L. Webb, and H. C. Yick, J. Org. Chem.,47, 1824 (1982).

    Google Scholar 

  31. S. R. Ramakumar, K. Venkatesan, and H. P. Weber, Helv. Chim. Acta,60, 1691 (1977).

    Google Scholar 

  32. P. Crabbe, Introduction to Chiroptical Methods in Chemistry [Russian translation], Mir, Moscow (1974), p. 168.

    Google Scholar 

  33. D. N. Kirk, Tetrahedron,42, 777 (1986).

    Google Scholar 

  34. H. Takayanagi, I. Hara, M. Goto, and H. Ogura, Croat. Chem. Acta,62(2A), 89 (1989).

    Google Scholar 

  35. H. Ogura, H. Takayanagi, K. Kubo, and K. Furuhata, J. Am. Chem. Soc.,95, 8056 (1973).

    Google Scholar 

  36. M. Kajtar, J. Kajtar, J. Rohricht, and J. G. Angyan, Croat. Chem. Acta,62(2A), 245 (1989).

    Google Scholar 

  37. H. Ogura, K. Takeda, and H. Takahashi, Chem. Pharm. Bull.,23, 2469 (1975).

    PubMed  Google Scholar 

  38. H. Ogura, H. Takayanagi, and K. Furuhata, J. Chem. Soc., Perkin Trans. 1, No. 6, 665 (1976).

  39. V. V. Dunina, E. G. Rukahdze, and V. M. Potapov, Preparation and Investigation of Optically Active Compounds [in Russian], Izd. Moskovsk. Gos. Univ., Moscow (1979).

    Google Scholar 

  40. G. G. De Angelis and W. C. Wildman, Tetrahedron,25, 5099 (1969).

    Google Scholar 

  41. W. C. Johnson, L. P. Fontana, and H. E. Smith, J. Am. Chem. Soc.,109, 3361 (1987).

    Google Scholar 

  42. V. G. Snatzke, Angew. Chem.,91, 380 (1979).

    Google Scholar 

  43. H. E. Smith, Croat. Chem. Acta,62(2A), 201 (1989).

    Google Scholar 

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Authors
  1. V. V. Dunina
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  2. N. N. Romanova
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Additional information

Communication 1, see ref. [1].

M. V. Lomonosov Moscow State University, 119899 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1059–1077, August, 1995. Original article submitted July 29, 1995.

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Dunina, V.V., Romanova, N.N. Synthesis and stereochemistry of chiral 2-azetidinones and 2-azetidinethiones. 2.* Study of the chiroptical properties of some 2-azetidinones. Chem Heterocycl Compd 31, 922–937 (1995). https://doi.org/10.1007/BF01170320

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