Kowalski ester homologation

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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[edit]

Proposed mechanism of the Kowalski ester homologation

The mechanism is disputed.

Variations[edit]

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[edit]

  1. ^ Kowalski, C. J.; Haque, M. S.; Fields, K. W. J. Am. Chem. Soc. 1985, 107, 1429. (doi:10.1021/ja00291a063)
  2. ^ Organic Syntheses, Coll. Vol. 9, p.426 (1998); Vol. 71, p.146 (1993). (Article)

See also[edit]