Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to β-Silyl Enones with Molecular Dioxygen
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- 作者：Jih Ru Hwu ; Chien Hsien Chen ; Chuan-I Hsu ; Asish R. Das ; Yen Cheng Li ; Lung Ching Lin
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：May 15, 2008
- 年：2008
- 卷：10
- 期：10
- 页码：1913 - 1916
- 全文大小：280K
- 年卷期：v.10,no.10(May 15, 2008)
- ISSN：1523-7052
文摘
Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 °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.