Silyl enol ether

Silyl enol ethers in organic chemistry are a class of organic compounds sharing a common functional group comprised of an enolate bonded through its oxygen terminus to an organosilicon group.

Silyl enol ethers are important intermediates in organic synthesis.

Organic synthesis

 * Trimethylsilyl enol ethers can be prepared from ketones in presence of a strong base and trimethylsilyl chloride.
 * Silyl enol ether can form by capturing any enolate formed in a nucleophilic conjugate addition.

Organic reactions
Silyl enol ethers react as nucleophiles in:
 * Aldol reactions
 * Michael reactions
 * Alkylations
 * Haloketone formation with halogens
 * Acyloin formation by organic oxidation with mCPBA

Saegusa oxidation
In the Saegusa oxidation certain silyl enol ethers are oxidized to enones with palladium(II) acetate. In the original publication the amount of palladium is less than stochiometric and 1,4-benzoquinone is used as sacrificial catalyst. The intermediate is an oxo-allylpalladium complex.


 * [[Image:SaegusaOxidation.png|350px|Saegusa oxidation]]

In one application an dienenone is synthesized in two steps from a cyclohexanone :


 * [[Image:SaegusaApplication.png|400px|Saegusa application Clive 2007]]