Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangements

4-Hydroxycyclopentenones represent a privileged scaffold in chemical synthesis. A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols to 4-hydroxycyclopentenones via a 4 pi electrocyclization has been developed. The catalytic Piancatelli rearrangement affords a single trans-diastereomer from both aryl and alkyl substituted furylcarbinols. Published by Elsevier Ltd.