Efficient synthesis of 4-hydroxycyclopentenones: Dysprosium(III) triflate catalyzed Piancatelli rearrangement
- Author(s): Fisher, D
- Palmer, LI
- Cook, JE
- Davis, JE
- Read De Alaniz, J
- et al.
Published Web Locationhttps://doi.org/10.1016/j.tet.2014.03.007
4-Hydroxycyclopentenones represent a privileged scaffold in chemical synthesis. A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols to 4-hydroxycyclopentenones via a 4π electrocyclization has been developed. The catalytic Piancatelli rearrangement affords a single trans-diastereomer from both aryl and alkyl substituted furylcarbinols.