Kowalski ester homologation

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

The Kowalski ester homologation

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
Proposed mechanism of the Kowalski ester homologation

The mechanism is disputed.

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.

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See also

References
  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: 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.; Collective Volume, 9, p. 426
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