Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl
Ting-Zhi Yao1, Yi-Cheng Tseng1, Jia-Luo Li1
1Department of Chemistry, Chung Yuan Christian University, Chung-Li 320314, Taiwan.
Abstract:
This study explores the selective oxidative scission of bicyclo[2.2.2]octenones derived from masked o-benzoquinones (MOBs). By employing the fragmentation of ketoximes and Schmidt-type reactions, we achieved the cleavage of α-dimethoxy carbonyl groups to yield highly functionalized cyclohexene frameworks, showcasing the expanding synthetic utility of bicyclo[2.2.2]octenones in complex organic synthesis. The methodologies developed are anticipated to contribute to advancements in organic and pharmaceutical chemistry.
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