title: Silicon-induced ene-type reaction in the thermal conversion of enolates to beta-silyl enones with molecular dioxygen.
abstract: 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.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, Republic of China. jrhwu@mx.nthu.edu.tw
authors.forename: Jih Ru
authors.initials: JR
authors.lastname: Hwu
authors.forename: Chien Hsien
authors.initials: CH
authors.lastname: Chen
authors.forename: Chuan-I
authors.initials: CI
authors.lastname: Hsu
authors.forename: Asish R
authors.initials: AR
authors.lastname: Das
authors.forename: Yen Cheng
authors.initials: YC
authors.lastname: Li
authors.forename: Lung Ching
authors.initials: LC
authors.lastname: Lin