Skip to main content
Log in

Asymmetrical nitrogen. 51. Synthesis and optical activation of 1,6-diazabicyclo-[3.1.0]hexane-5-carboxylic acid and its derivatives

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Total separation of the (−)-1S,5R,6S- and (+)-1R,5S,6R-enantiomers of the stable l,6-diazabicyclo[3.1.0]hexane-5-carboxylic acid is effected via the diastereoisomeric salts with l-ephedrine.

  2. 2.

    The diastereoisomeric α-phenylethylamides of l,6-diazabicyclo[3.1.0]hexane-5-carboxylic acid have been obtained in relatively low optical purity (10–12%) by amidating the methyl esters followed by recrystallization and the asymmetric epimination of Δ1-pyrroline-2-carboxylic acid S-α-phenylethylamide.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. G. V. Shustov, S. N. Denisenko, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1831 (1986).

  2. R. G. Kostyanovskii, G. V. Shustov, O. G. Nabiev, S. N. Denisenko, S. A. Sukhanova, and É. F. Lavretskaya, Khim.-Farm. Zh., 671 (1986).

  3. G. V. Shustov, S. A. D'yachenko, S. M. Aldoshin, A. B. Zolotoi, M. G. Isobaev, I. I. Chervin, L. O. Atovmyan, and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,231, 1174 (1976).

    Google Scholar 

  4. R. G. Kostyanovsky (Kostyanovskii), G. V. Shustov, and N. L. Zaichenko, Tetrahedron,38, 1949 (1982).

    Google Scholar 

  5. G. V. Shustov, A. B. Zolotoi, O. A. Dyachenko (D'yachenko), L. O. Atovmyan, and T. G. Kostyanovsky (Kostyanovskii), Tetrahedron,40, 2151 (1984).

    Google Scholar 

  6. R. G. Kostyanovskii and G. V. Shustov, Dokl. Akad. Nauk SSSR,232, 1081 (1977).

    Google Scholar 

  7. S. H. Wilen, Top. Stereochem.,6, 107 (1971).

    Google Scholar 

  8. I. Idzumi and A. Tai, Stereodifferentiating Reactions [Russian translation], Mir, Moscow (1979).

    Google Scholar 

  9. V. I. Sokolov, An Introduction to Theoretical Stereochemistry [in Russian], Nauka, Moscow (1979).

    Google Scholar 

  10. V. F. Bystrov, Uspekhi Khimii,43, 512 (1972).

    Google Scholar 

  11. M. Cherest and J. Felkin, Tetrahedron Lett., 2201 (1968).

  12. N. T. Anh and O. Eisenstein, Nouv. J. Chim.,1, 61 (1977).

    Google Scholar 

  13. W. E. Pereira and B. Halpern, Austral. J. Chem.,25, 667 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10 pp. 2266–2271, October, 1986.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shustov, G.V., Denisenko, S.N., Zolotoi, A.B. et al. Asymmetrical nitrogen. 51. Synthesis and optical activation of 1,6-diazabicyclo-[3.1.0]hexane-5-carboxylic acid and its derivatives. Russ Chem Bull 35, 2071–2076 (1986). https://doi.org/10.1007/BF00957527

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00957527

Keywords

Navigation