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Recent progress in the synthesis of aziridine derivatives (microreview)

  • HETEROCYCLES IN FOCUS
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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. (a) Gabriel, S. Ber. Dtsch. Chem. Ges. 1888, 21, 1049. (b) Gabriel, S. Ber. Dtsch. Chem. Ges. 1888, 21, 2664.

  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.

  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.

  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.

  5. Chen, J.; Yan, W.-Q.; Lam, C. M.; Zeng, C.-C.; Hu, L.-M.; Little, R. D. Org. Lett. 2015, 17, 986.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  7. Hajra, S.; Aziz, S. M.; Jana, B.; Mahish, P.; Das, D. Org. Lett. 2016, 18, 532.

    Article  CAS  Google Scholar 

  8. Rigoli, J. W.; Weatherly, C. D.; Vo, B. T.; Neale, S.; Meis, A. R.; Schomaker, J. M. Org. Lett. 2013, 15, 290.

    Article  CAS  Google Scholar 

  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.

  10. Tao, J.; Jin, L.-M.; Zhang, X. P. Beilstein J. Org. Chem. 2014, 10, 1282.

    Article  Google Scholar 

  11. Huang, Z.-A.; Liu, H.; Lu, C.-D.; Xu, Y.-J. Org. Lett. 2015, 17, 4042.

    Article  CAS  Google Scholar 

  12. Jiang, J.; Liu, H.; Lu, C.-D.; Xu, Y.-J. Org. Lett. 2016, 18, 880.

    Article  CAS  Google Scholar 

  13. Moragas, T.; Churcher, I.; Lewis, W.; Stockman, R. A. Org. Lett. 2014, 16, 6290.

    Article  CAS  Google Scholar 

  14. Reddy, A. R.; Zhou, C.-Y.; Che, C.-M. Org. Lett. 2014, 16, 1048.

    Article  CAS  Google Scholar 

  15. Armstrong, A.; Pullin, R. D. C.; Scutt, J. N. Synlett 2016, 27, 151.

    Article  CAS  Google Scholar 

  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.

  17. Molnár, I. G.; Tanzer, E.-M.; Daniliuc, C.; Gilmour, R. Chem.– Eur. J. 2014, 20, 794.

    Article  Google Scholar 

  18. Lai, B.-N.; Qiu, J.-F.; Zhang, H.-X.; Nie, J.; Ma, J.-A. Org. Lett. 2016, 18, 520.

    Article  CAS  Google Scholar 

  19. Huang, M.-T.; Wu, H.-Y.; Chein, R.-J. Chem. Commun. 2014, 50, 1101.

    Article  CAS  Google Scholar 

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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).

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Correspondence to Szymon Jarzyński.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(6), 353–355

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Jarzyński, S., Leśniak, S. Recent progress in the synthesis of aziridine derivatives (microreview). Chem Heterocycl Comp 52, 353–355 (2016). https://doi.org/10.1007/s10593-016-1893-8

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  • DOI: https://doi.org/10.1007/s10593-016-1893-8

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