Trans-Selective Carboxylative Cyclization of 1,6-Dienes Using the CO2 Radical Anion

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-07-27 DOI:10.1093/chemle/upae149

Yan Song, Hiroki Hayashi, Saeesh R Mangaonkar, Tsuyoshi Mita

引用次数: 0

Abstract

The reactivity of the carbon dioxide radical anion (CO2•−) toward alkenes has garnered remarkable attention owing to its potential to synthesize valuable organic compounds. Herein, we report the reactions between CO2•− and 1,6-dienes, yielding 5-membered lactam derivatives via highly trans-selective 5-exo-trig cyclization. Both carboxylative cyclization and hydrocyclization occur with up to 74% combined yield. Computational studies show that the transition state during cyclization favors the trans-configuration over cis. This work offers new insights into the synthesis of N-heterocycles.

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利用二氧化碳自由基阴离子对 1,6-二烯进行反选择性羧基环化反应

由于二氧化碳自由基阴离子（CO2--）具有合成有价值有机化合物的潜力，因此它与烯烃的反应性备受关注。在此，我们报告了 CO2--与 1,6-二烯之间的反应，通过高度反式选择性的 5-外三环化反应生成 5 元内酰胺衍生物。羧基环化和加氢环化的综合产率高达 74%。计算研究表明，环化过程中的过渡态有利于反式构型而非顺式构型。这项工作为合成 N-杂环提供了新的见解。

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

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.