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Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to b-Silyl Enones with Molecular Dioxygen.

  作者 Hwu, Jih Ru;Chen, Chien Hsien;Hsu, Chuan-I.;Das, Asish R.;Li, Yen Cheng;Lin, Lung Ching;  
  选自 期刊  Organic Letters;  卷期  2008年10-10;  页码  1913-1916  
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[摘要]Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with mol. dioxygen in toluene at 110? 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 iso-Pr group. These results indicate the existence of an unprecedented Si-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.

 
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