Blum-Ittah Aziridine Synthesis

Blum-Ittah Aziridine Synthesis

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  • General Characteristics

Epoxides can be converted into aziridines by nucleophilic attack of azide ion, the Staudinger reaction, and aziridine ring formation with elimination of triphenylphosphine oxide.

  • General References

  • Ittah, Y.; Shahak, I.; Blum, J. J. Org. Chem. 197843, 397. DOI: 10.1021/jo00397a004
  • Ittah, Y.; Sasson, Y.; Shahak, I.; Tsaroom, S.; Blum. J. J. Org. Chem. 1978, 43, 4271. DOI: 10.1021/jo00416a003
  • Reaction Mechanism

The Staudinger azide reduction and elimination of PPh3=O leads to the formation of aziridines. Note that both C-N bond forming steps are stereospecific SN2 displacement.


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  • External Links

Aziridines in Synthesis (PDF, Baran’s group)