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Use of azetidine scaffolds in stereoselective transformations (microreview)

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. Diethelm, S.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 8500.

    Article  CAS  PubMed  Google Scholar 

  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.

  3. Antermite, D.; Degennaro, L.; Luisi, R. Org. Biomol. Chem. 2017, 15, 34.

    Article  CAS  Google Scholar 

  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.

  5. Brandi, A.; Cicchi S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988.

    Article  CAS  PubMed  Google Scholar 

  6. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gómez-Campillos, G. Adv. Synth. Catal. 2013, 355, 2089.

    Article  CAS  Google Scholar 

  7. Sakamoto, R.; Inada, T.; Sakurai, S.; Maruoka, K. Org. Lett. 2016, 18, 6252.

    Article  CAS  PubMed  Google Scholar 

  8. Jasinski, M.; Moreno-Clavijo, E.; Reissig, H. U. Eur. J. Org. Chem. 2014, 442.

  9. Hodgson, D. M.; Mortimer, C. L.; McKenna, J. M. Org. Lett. 2015, 17, 330.

    Article  CAS  PubMed  Google Scholar 

  10. Degennaro, L.; Zenzola, M.; Trinchera, P.; Carroccia, L.; Giovine, A.; Romanazzi, G.; Falcicchio, A.; Luisi, R. Chem. Commun. 2014, 50, 1698.

    Article  CAS  Google Scholar 

  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.

  12. Parisi, G.; Capitanelli, E.; Pierro, A.; Romanazzi, G.; Clarkson, G. J.; Degennaro, L.; Luisi, R. Chem. Commun. 2015, 51, 15588.

    Article  CAS  Google Scholar 

  13. Tayama, E.; Watanabe K.; Sotome, S. Org. Biomol. Chem. 2017, 15, 6668.

    Article  CAS  PubMed  Google Scholar 

  14. Music, A.; Baumann, A. N.; Eisold, M.; Didier D. J. Org. Chem. 2018, 83, 783.

    Article  CAS  PubMed  Google Scholar 

  15. Han, S.; Zard, S. Z. Tetrahedron 2015, 71, 3680.

    Article  CAS  Google Scholar 

  16. Moni, L.; Banfi, L.; Basso, A.; Bozzano, A.; Spallarossa, M.; Wessjohann, L.; Riva, R. Molecules 2016, 21, 1153.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Reidl, T. W.; Son, J.; Wink, D. J.; Anderson, L. L. Angew. Chem., Int. Ed. 2017, 56, 11579.

    Article  CAS  Google Scholar 

  19. Dowling, M. S.; Fernando, D. P.; Hou, J.; Liu, B.; Smith, A. C. J. Org. Chem. 2016, 81, 3031.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmacy – Pharmaceutical Sciences, University of Bari Aldo Moro, FLAME-Lab – Flow Chemistry and Microreactor Technology Laboratory, Via E. Orabona 4, 70125, Bari, Italy

    Renzo Luisi & Leonardo Degennaro

Authors
  1. Renzo Luisi
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  2. Leonardo Degennaro
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Correspondence to Leonardo Degennaro.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 400–402

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Luisi, R., Degennaro, L. Use of azetidine scaffolds in stereoselective transformations (microreview). Chem Heterocycl Comp 54, 400–402 (2018). https://doi.org/10.1007/s10593-018-2283-1

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  • DOI: https://doi.org/10.1007/s10593-018-2283-1

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