Kowalski ester homologation
- Kowalski ester homologation
The Kowalski ester homologation is a chemical reaction for the homologation of esters. [Kowalski, C. J.; Haque, M. S.; Fields, K. W. "J. Am. Chem. Soc." 1985, "107", 1429. (DOI|10.1021/ja00291a063)] ["Organic Syntheses", Coll. Vol. 9, p.426 (1998); Vol. 71, p.146 (1993). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv9p0426 Article] )]
This reaction was designed as a safer alternative to the Arndt-Eistert synthesis. The Kowalski reaction is named after its inventor, Conrad J. Kowalski.
Reaction mechanism
The mechanism is disputed.
Variations
A modification of the procedure has been described that results in higher yields. [Smith III, A. B.; Kozmin, S. A.; Paone, D. V. "J. Am. Chem. Soc." 2000, "122", 4984. (DOI|10.1021/ja000430p)]
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.Fact|date=September 2007
References
See also
* Curtius rearrangement
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