Advertisement

Chemistry of Heterocyclic Compounds

, Volume 52, Issue 6, pp 353–355 | Cite as

Recent progress in the synthesis of aziridine derivatives (microreview)

  • Szymon Jarzyński
  • Stanisław Leśniak
HETEROCYCLES IN FOCUS
The goal of the present microreview is to cover the recent advances in the synthesis of aziridine derivatives. This review covers recent strategies (last 4 years) towards ethyleneimine via aziridination of alkenes and carbon-imine cyclization.

Keywords

Alkene Apply Chemistry Hydroxylamine Thermolysis Full Professor 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Authors thank the National Science Center (Cracow, Poland) for generous financial support within the project Preludium (Grant Preludium-8; UMO-2014/15/N/ST5/02897).

References

  1. 1.
    (a) Gabriel, S. Ber. Dtsch. Chem. Ges. 1888, 21, 1049. (b) Gabriel, S. Ber. Dtsch. Chem. Ges. 1888, 21, 2664.Google Scholar
  2. 2.
    (a) Callebaut, G.; Meiresonne, T.; De Kimpe, N.; Mangelinckx, S. Chem. Rev. 2014, 114, 7954. (b) Stankovic, S.; D'hooghe, M.; Catak, S.; Eum, H.; Waroquier, M.; Van Speybroeck, V.; De Kimpe, N.; Ha, H.-H. Chem. Soc. Rev. 2012, 41, 643.Google Scholar
  3. 3.
    (a) Pellissier, H. Tetrahedron 2010, 66, 1509. (b) Liu, P. Tetrahedron 2010, 66, 2549. (c) Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.Google Scholar
  4. 4.
    (a) Jarzyński, S.; Leśniak, S.; Pieczonka, A. M.; Rachwalski, M. Tetrahedron: Asymmetry 2015, 26, 35. (b) Pieczonka, A. M.; Leśniak, S.; Jarzyński, S.; Rachwalski, M. Tetrahedron:Asymmetry 2015, 26, 148. (c) Song X.; Hua Y.-Z.; Shi J.-G.; Sun P.-P.; Wang M.-C.; Chang J. J. Org. Chem. 2014, 79, 6087.Google Scholar
  5. 5.
    Chen, J.; Yan, W.-Q.; Lam, C. M.; Zeng, C.-C.; Hu, L.-M.; Little, R. D. Org. Lett. 2015, 17, 986.CrossRefGoogle Scholar
  6. 6.
    Marsini, M. A.; Reeves, J. T.; Desrosiers, J.-N.; Herbage, M. A.; Savoie, J.; Li, Z.; Fandrick, K. R.; Sader, C. A.; McKibben, B.; Gao, D. A.; Cui, J.; Gonnella, N. C.; Lee, H.; Wei, X.; Roschangar, F.; Lu, B. Z.; Senanayake, C. H. Org. Lett. 2015, 17, 5614.CrossRefGoogle Scholar
  7. 7.
    Hajra, S.; Aziz, S. M.; Jana, B.; Mahish, P.; Das, D. Org. Lett. 2016, 18, 532.CrossRefGoogle Scholar
  8. 8.
    Rigoli, J. W.; Weatherly, C. D.; Vo, B. T.; Neale, S.; Meis, A. R.; Schomaker, J. M. Org. Lett. 2013, 15, 290.CrossRefGoogle Scholar
  9. 9.
    (a) Jin, L.-M.; Xu, X.; Lu, H.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2013, 52, 5309. (b) Jin, L.-M.; Xu, X.; Lu, H.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem. 2013, 125, 5417.Google Scholar
  10. 10.
    Tao, J.; Jin, L.-M.; Zhang, X. P. Beilstein J. Org. Chem. 2014, 10, 1282.CrossRefGoogle Scholar
  11. 11.
    Huang, Z.-A.; Liu, H.; Lu, C.-D.; Xu, Y.-J. Org. Lett. 2015, 17, 4042.CrossRefGoogle Scholar
  12. 12.
    Jiang, J.; Liu, H.; Lu, C.-D.; Xu, Y.-J. Org. Lett. 2016, 18, 880.CrossRefGoogle Scholar
  13. 13.
    Moragas, T.; Churcher, I.; Lewis, W.; Stockman, R. A. Org. Lett. 2014, 16, 6290.CrossRefGoogle Scholar
  14. 14.
    Reddy, A. R.; Zhou, C.-Y.; Che, C.-M. Org. Lett. 2014, 16, 1048.CrossRefGoogle Scholar
  15. 15.
    Armstrong, A.; Pullin, R. D. C.; Scutt, J. N. Synlett 2016, 27, 151.CrossRefGoogle Scholar
  16. 16.
    (a) Bencivenni, G.; Righi, P.; Lunazzi, L.; Ranieri, S.; Mancinelli, M.; Mazzanti, A. Chirality 2015, 27, 875. (b) Armstrong, A.; Pullin, R. D. C.; Jenner, C. R.; Foo, K.; White, A. J. P.; Scutt, J. N. Tetrahedron: Asymmetry 2014, 25, 74. (c) Rachwalski, M.; Wujkowska, Z.; Leśniak, S.; Kiełbasiński, P. ChemCatChem 2015, 7, 3589.Google Scholar
  17. 17.
    Molnár, I. G.; Tanzer, E.-M.; Daniliuc, C.; Gilmour, R. Chem.– Eur. J. 2014, 20, 794.CrossRefGoogle Scholar
  18. 18.
    Lai, B.-N.; Qiu, J.-F.; Zhang, H.-X.; Nie, J.; Ma, J.-A. Org. Lett. 2016, 18, 520.CrossRefGoogle Scholar
  19. 19.
    Huang, M.-T.; Wu, H.-Y.; Chein, R.-J. Chem. Commun. 2014, 50, 1101.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Faculty of ChemistryUniversity of ŁódźŁódźPoland

Personalised recommendations