☆ 4.8 Article

Silicon-induced ene-type reaction in the thermal conversion of enolates to β-silyl enones with molecular dioxygen

ORGANIC LETTERS (2008)

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ORGANIC LETTERS

卷 10, 期 10, 页码 1913-1916

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AMER CHEMICAL SOC

DOI: 10.1021/ol800007v

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Chemistry, Organic

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Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 degrees C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.

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