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Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 787–789 | Cite as

Unusual course of “enolate-imine” condensation in approach to β-lactams

  • Z. R. Valiullina
  • F. A. Gimalova
  • L. V. Spirikhin
  • M. S. Miftakhov
Short Communications

Abstract

In reaction of methyl (Е)-3-(methoxycarbonyl)methylimino-2,2-dimethylpropanoate with enolate of ethyl 3-hydroxybutanoate an abnormal reaction product was isolated, 2-methyl 4-ethyl-(2S*,3S*,4S*,5S*)-3-methyl-5-(2-methyl-1-methoxy-1-oxopropan-2-yl)pyrrolidine-2,4-dicarboxylate.

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References

  1. 1.
    Hart, D.J. and Ha, D.-Ch., Chem. Rev., 1989, vol. 89, p. 1447. doi 10.1021/cr00097a003CrossRefGoogle Scholar
  2. 2.
    Fu, N. and Tidwell, T.T., Tetrahedron, 2008, vol. 64, p. 10465. doi 10.1016/j.tet.2008.08.028CrossRefGoogle Scholar
  3. 3.
    Brandi, A., Cicchi, S., and Cordero, F.M., Chem. Rev., 2008, vol. 108, p. 3988. doi 10.1021/cr800325eCrossRefGoogle Scholar
  4. 4.
    Orbegozo, T., Burel, F., Jubault, P., and Pannecoucke, X., Tetrahedron, 2013, vol. 69, p. 4015. doi 10.1016/j.tet.2013.02.043CrossRefGoogle Scholar
  5. 5.
    Betts, J.W., Phee, L.M., Abdul Momin, M.H.F., Umland, K.-D., Brem, J., Schofield, C.J., and Wareham, D.W., Med. Chem. Commun., 2016, vol. 7, p. 190. doi 10.1039/C5MD00380FCrossRefGoogle Scholar
  6. 6.
    Georg, G.I., Kant, J., and Gill, H.S., J. Am. Chem. Soc., 1987, vol. 109, p. 1129. doi 10.1021/ja00238a023CrossRefGoogle Scholar
  7. 7.
    Tanimoto, S., Kokubo, T., Oida, T., and Ikehira, H., Synthesis, 1982, p. 723. doi 10.1055/s-1982-29913Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • Z. R. Valiullina
    • 1
  • F. A. Gimalova
    • 1
  • L. V. Spirikhin
    • 1
  • M. S. Miftakhov
    • 1
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfaRussia

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