Efficient synthesis of 4-hydroxycyclopentenones: Dysprosium(III) triflate catalyzed Piancatelli rearrangement
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.