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Open Access Publications from the University of California

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.

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.

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