Introduction of Different Groups to α- and β-Positions of Cyclic α,β-Unsaturated Ketones via [2π + 2π] Photocycloaddition with Ketene Silyl Acetals Followed by Electrode Reaction
acetylenedicarboxylate is reacted with ketene alkyl trimethylsilyl acetals in the presence of a catalytic amount of zirconiumtetrachloride, dimethyl 2-alkoxycarbonyl-3-alkylidenebutanedioates are afforded. Although the silyl enol ether from acetophenone undergoes the same type of reaction, other trisubstituted silyl enol ethers such as those from butyrophenone and 3-pentanone fail to react with dimethyl
Introduction of Different Groups to α- and β-Positions of Cyclic α,β-Unsaturated Ketones via [2π + 2π] Photocycloaddition with Ketene Silyl Acetals Followed by Electrode Reaction
作者:Michiharu Mitani、Yosinari Osakabe、Junji Hamano
DOI:10.1246/cl.1994.1255
日期:1994.7
The photoadducts of cyclic conjugated enones with ketene silyl acetals and silyl enol ether were subjected to electrolysis to bring about the oxidative cleavage of the Si-O bond, which induced the collapse of the cyclobutane ring to perform the introduction of the different groups to both positions of the ene moieties of the enones.