Advertisement

Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 400–402 | Cite as

Open image in new window Use of azetidine scaffolds in stereoselective transformations (microreview)

  • Renzo Luisi
  • Leonardo Degennaro
Article

Open image in new window Noteworthy stereoselective approaches toward the synthesis of densely substituted azetidines are reported. This microreview covers a selection of the latest efficient methods for the functionalization of azetidine cores by metalation, C–H activation, radical or biocatalytic processes, as well as nonclassical and large-scale preparative procedures.

References

  1. 1.
    Diethelm, S.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 8500.CrossRefPubMedGoogle Scholar
  2. 2.
    Yoda, H.; Takahashi, M.; Sengoku, T. Heterocycles in Natural Product Synthesis; Majumdar, K. C.; Chattopadhyay, S. K., Eds.; Wiley-VCH: Weinheim, 2011, 1st ed., p. 41.Google Scholar
  3. 3.
    Antermite, D.; Degennaro, L.; Luisi, R. Org. Biomol. Chem. 2017, 15, 34.CrossRefGoogle Scholar
  4. 4.
    Rousseau, G.; Robin, S. In Modern Heterocyclic Chemistry; Alvárez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH: Weinheim, 2011, 1st ed., vol. 1, p. 163.Google Scholar
  5. 5.
    Brandi, A.; Cicchi S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988.CrossRefPubMedGoogle Scholar
  6. 6.
    Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gómez-Campillos, G. Adv. Synth. Catal. 2013, 355, 2089.CrossRefGoogle Scholar
  7. 7.
    Sakamoto, R.; Inada, T.; Sakurai, S.; Maruoka, K. Org. Lett. 2016, 18, 6252.CrossRefPubMedGoogle Scholar
  8. 8.
    Jasinski, M.; Moreno-Clavijo, E.; Reissig, H. U. Eur. J. Org. Chem. 2014, 442.Google Scholar
  9. 9.
    Hodgson, D. M.; Mortimer, C. L.; McKenna, J. M. Org. Lett. 2015, 17, 330.CrossRefPubMedGoogle Scholar
  10. 10.
    Degennaro, L.; Zenzola, M.; Trinchera, P.; Carroccia, L.; Giovine, A.; Romanazzi, G.; Falcicchio, A.; Luisi, R. Chem. Commun. 2014, 50, 1698.CrossRefGoogle Scholar
  11. 11.
    Zenzola, M.; Degennaro, L.; Trinchera, P.; Carroccia, L.; Giovine, A.; Romanazzi, G.; Mastrorilli, P.; Rizzi, R.; Pisano, L.; Luisi, R. Chem.–Eur. J. 2014, 20, 12190.Google Scholar
  12. 12.
    Parisi, G.; Capitanelli, E.; Pierro, A.; Romanazzi, G.; Clarkson, G. J.; Degennaro, L.; Luisi, R. Chem. Commun. 2015, 51, 15588.CrossRefGoogle Scholar
  13. 13.
    Tayama, E.; Watanabe K.; Sotome, S. Org. Biomol. Chem. 2017, 15, 6668.CrossRefPubMedGoogle Scholar
  14. 14.
    Music, A.; Baumann, A. N.; Eisold, M.; Didier D. J. Org. Chem. 2018, 83, 783.CrossRefPubMedGoogle Scholar
  15. 15.
    Han, S.; Zard, S. Z. Tetrahedron 2015, 71, 3680.CrossRefGoogle Scholar
  16. 16.
    Moni, L.; Banfi, L.; Basso, A.; Bozzano, A.; Spallarossa, M.; Wessjohann, L.; Riva, R. Molecules 2016, 21, 1153.CrossRefGoogle Scholar
  17. 17.
    Maetani, M.; Zoller, J.; Melillo, B.; Verho, O.; Kato, N.; Pu, J.; Comer, E.; Schreiber, S. L. J. Am. Chem. Soc. 2017, 139, 11300.CrossRefPubMedPubMedCentralGoogle Scholar
  18. 18.
    Reidl, T. W.; Son, J.; Wink, D. J.; Anderson, L. L. Angew. Chem., Int. Ed. 2017, 56, 11579.CrossRefGoogle Scholar
  19. 19.
    Dowling, M. S.; Fernando, D. P.; Hou, J.; Liu, B.; Smith, A. C. J. Org. Chem. 2016, 81, 3031.CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Pharmacy – Pharmaceutical SciencesUniversity of Bari Aldo Moro, FLAME-Lab – Flow Chemistry and Microreactor Technology LaboratoryBariItaly

Personalised recommendations