Piancatelli rearrangement

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

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

References

  1. ^ G. Piancatelli, A. Scettri, S. Barbadoro, Tetrahedron Lett. 1976, 17, 3555.
  2. ^ A. N. Faza, C. S. Lopez, R. Alvarez, I. R. de Lera, Chem. Eur. J.2004, 10, 4324.
  3. ^ Gesine K. Veits, Donald R. Wenz, and Javier Read de Alaniz, Angew. Chem. Int. Ed. 2010, 49, 9484.