Aliphatic Ketone Claisen Rearrangement: Troubleshooting the Transetherification Step by Identifying a Stable Acid Catalyst

Veera K. Bruce, Kaveh Farshadfar, Aino Rolig, Kari Laasonen, Petri M. Pihko*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

After optimization for retention of catalytic activity, 4-chlorobenzoic acid emerged as the optimal catalyst for the aliphatic ketone Claisen rearrangement. The optimal catalyst enables a one-pot, metal-free, catalytic protocol from allylic alcohols to γ,δ-unsaturated ketones. The optimized process tolerates a range of substrates, including substituents with acid-labile protecting groups. Reaction monitoring and DFT studies of the aliphatic ketone Claisen process agree that the ultimate rearrangement step typically has the highest activation barrier.

Original languageEnglish
Article numbere202402371
Number of pages6
JournalChemistry - A European Journal
Volume30
Issue number53
DOIs
Publication statusPublished - 19 Sept 2024
MoE publication typeA1 Journal article-refereed

Keywords

  • Acid catalysis
  • Claisen rearrangement
  • Reaction optimization

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