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Kowalski ester homologation
The Kowalski ester homologation is a chemical reaction for the homologation of esters.
This reaction was designed as a safer alternative to the Arndt–Eistert synthesis, avoiding the need for diazomethane. The Kowalski reaction is named after its inventor, Conrad J. Kowalski.
Reaction mechanism
The mechanism is disputed. Enolate formation Ester is deprotonated at the α-position → enolate anion.
CH₂ insertion Enolate reacts with dihalomethane → introduces a –CH₂– group.
Rearrangement and stabilization Under basic conditions → homologated ester forms.
Variations
By changing the reagent in the second step of the reaction, the Kowalski ester homologation can also be used for the preparation of silyl ynol ethers.
References
References
- (1985). "Ester homologation via α-bromo α-keto dianion rearrangement". [[J. Am. Chem. Soc.]].
- (1993). "Ethyl 1-naphthylacetate: ester homologation via ynolate anions".
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