The Ireland-Claisen (also known as the ester enolate Claisen rearrangement) uses lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCI), sodium hydroxide, and water to convert an allyl ester to a γ, δ-unsaturated carboxylic acid. The α-hydrogen of the allyl ester is deprotonated by LDA, creating an enolate, which attacks TMSCl, releasing LiCl salt. A [3,3]-sigmatropic rearrangement, followed by the removal of the TMS group produces the final γ, δ-unsaturated carboxylic acid.


Top Citations

Original Paper

Related Reactions

  • Claisen Rearrangement
  • Cope Rearrangement

Related Compounds

  • LDA
  • NaOH (CAS 1310-73-2)
  • Allyl Ester
By shuhan yang


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