Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-01-28 DOI:10.1021/acs.joc.4c0269910.1021/acs.joc.4c02699

Ting-Zhi Yao, Yi-Cheng Tseng, Jia-Luo Li, Deng-Lian Hou and Gary Jing Chuang*,

引用次数: 0

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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双环[2.2.2]辛烯酮的氧化裂解：解开α-二甲氧基

本研究探讨了由掩膜邻苯醌（MOBs）衍生的双环[2.2.2]辛烯酮的选择性氧化裂解。通过酮肟的裂解和施密特型反应，我们实现了α-二甲氧基羰基的裂解，得到了高功能化的环己烯框架，展示了双环[2.2.2]辛烯酮在复杂有机合成中的广泛应用。所开发的方法预计将有助于有机化学和药物化学的进步。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.