Kowalski ester homologation

The Kowalski ester homologation is a chemical reaction for the homologation of esters.^[1]^[2]

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.^{[further explanation needed]}

Variations

Proposed mechanism of the Kowalski ester homologation

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.^{[citation needed]}

References

^ Kowalski, C. J.; Haque, M. S.; Fields, K. W. (1985). "Ester homologation via α-bromo α-keto dianion rearrangement". J. Am. Chem. Soc. 107 (5): 1429–1430. doi:10.1021/ja00291a063.
^ Reddy, R. E.; Kowalski, C. J. (1993). "Ethyl 1-naphthylacetate: ester homologation via ynolate anions". Organic Syntheses. 71: 146; Collected Volumes, vol. 9, p. 426.

[1] Kowalski, C. J.; Haque, M. S.; Fields, K. W. (1985). "Ester homologation via α-bromo α-keto dianion rearrangement". J. Am. Chem. Soc. 107 (5): 1429–1430. doi:10.1021/ja00291a063.

[2] Reddy, R. E.; Kowalski, C. J. (1993). "Ethyl 1-naphthylacetate: ester homologation via ynolate anions". Organic Syntheses. 71: 146; Collected Volumes, vol. 9, p. 426.

[1]

[2]

Kowalski ester homologation

Reaction mechanism

Variations

See also

References