Piancatelli rearrangement

In 1976, the Italian chemist G. Piancatelli and co-workers developed a new method to synthesize the 4-hydroxycyclopentenone derivatives from suitable 2-furylcarbinols through an acid-catalyzed rearrangement:[1]

The mechanism of this reaction is believed to be a 4-pi electrocyclization, analogous to the Nazarov cyclization reaction.[2][3]

References

  1. ↑ G. Piancatelli, A. Scettri, S. Barbadoro (1976). "A useful preparation of 4-substituted 5-hydroxy-3-oxocyclopentene". Tetrahedron Lett. 17 (39): 3555. doi:10.1016/S0040-4039(00)71357-8.
  2. ↑ A. N. Faza, C. S. Lopez, R. Alvarez, I. R. de Lera (2004). "Theoretical study of the electrocyclic ring closure of hydroxypentadienyl cations". Chem. Eur. J. 10 (17): 4324–33. doi:10.1002/chem.200400037. PMID 15352115.
  3. ↑ Gesine K. Veits, Donald R. Wenz, and Javier Read de Alaniz (2010). "Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement". Angew. Chem. Int. Ed. 49 (49): 9484. doi:10.1002/anie.201005131.