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