Claisen carbonyl condensation
An ester enolate attacks another suitable ester carbonyl.
Key knowledge
An ester enolate attacks another suitable ester carbonyl. The tetrahedral intermediate expels an alkoxide, giving a β-keto ester rather than an aldol alcohol. In the classical self-condensation, deprotonation of the acidic product helps drive formation and accounts for stoichiometric base consumption.
Conditions and scope
- The classical driven self-condensation requires appropriate α hydrogens and a compatible base/leaving group.
- Mixed condensations and substrates lacking the product proton require separate selectivity and driving-force analysis.
Sources · 1
References
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Evidence and review
Read tetrahedral-intermediate/alkoxide-loss contrast with aldol and α-hydrogen/product-deprotonation requirement.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-claisen-condensation
- Revision
- core.1
- Structured reference record
- University core expansion