The rearrangement of furylcarbinols with nitrogen and oxygen nucleophiles allows highly efficient access to highly valuable 4-substituted cyclopentenones in a stereoselective manner. Our group has explored the aza-Piancatelli and oxa-Piancatelli rearrangements using dysprosium trifluoromethanesulfonate as the catalyst. Furylcarbinols are readily accessed from cheap, naturally abundant furan derivatives. Mechanistic insights as well as the scope and applications of this transformation will be detailed. 

Rearrangements of furylcarbinols to substituted cyclopentenones

245th National Meeting (2013)

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