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.

• Reagents: LDA, TMSCl, NaOH, Water
• Reactant: Allyl Ester
• Product: γ, δ-Unsaturated Carboxylic Acid
• Type of Reaction: Rearrangement

Mechanism

Original Paper

Top Citations

Related Reactions

Related Compounds