Synthesis of Vinyl Azetidines and β-Lactams from Allenamides via Energy-Transfer Relay

Abstract

Azetidines and β-lactams are useful and versatile building blocks with ample synthetic applications and pharmaceutical uses. However, few catalytic methods provide densely functionalized monocyclic derivatives, and none could easily afford both azetidines and β-lactams. Herein, we solved this issue with allenamides. The challenging substrates were activated by energy transfer combining a tailor-made Ir(III) complex and a binaphthyl cocatalyst, which acts as a triplet-state relay and stabilizes intermediates via dispersion interactions. A triplet intermediate with a vinyl-radical character gives the strained heterocycles upon 1,5 hydrogen atom transfer. Products have a congested all-carbon quaternary center and a useful allylamine unit and are prepared at room temperature with complete atom economy. The utility of the method is shown by further downstream derivatization.

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BibTeX RIS

BibTeX

@article{sparascio2026synthesis,
  title = {{Synthesis of Vinyl Azetidines and β-Lactams from Allenamides via Energy-Transfer Relay}},
  author = {Sara Sparascio and Gabriele Scarica and Alessandro Cerveri and Giulia Russo and Davide Spataro and Luciano Marchiò and Matteo Lanzi and Giovanni Maestri},
  journal = {ACS Catalysis},
  year = {2026},
  month = oct,
  doi = {10.1021/acscatal.5c04424},
  url = {https://hal.science/hal-05793506v1},
  note = {CC BY 4.0},
}

RIS

TY  - JOUR
TI  - Synthesis of Vinyl Azetidines and β-Lactams from Allenamides via Energy-Transfer Relay
AU  - Sara Sparascio
AU  - Gabriele Scarica
AU  - Alessandro Cerveri
AU  - Giulia Russo
AU  - Davide Spataro
AU  - Luciano Marchiò
AU  - Matteo Lanzi
AU  - Giovanni Maestri
PY  - 2026
DA  - 2026/10/12
JO  - ACS Catalysis
DO  - 10.1021/acscatal.5c04424
UR  - https://hal.science/hal-05793506v1
AB  - Azetidines and β-lactams are useful and versatile building blocks with ample synthetic applications and pharmaceutical uses. However, few catalytic methods provide densely functionalized monocyclic derivatives, and none could easily afford both azetidines and β-lactams. Herein, we solved this issue with allenamides. The challenging substrates were activated by energy transfer combining a tailor-made Ir(III) complex and a binaphthyl cocatalyst, which acts as a triplet-state relay and stabilizes intermediates via dispersion interactions. A triplet intermediate with a vinyl-radical character gives the strained heterocycles upon 1,5 hydrogen atom transfer. Products have a congested all-carbon quaternary center and a useful allylamine unit and are prepared at room temperature with complete atom economy. The utility of the method is shown by further downstream derivatization.
SN  - 2155-5435
SN  - 2155-5435
ER  -

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