Yan Song, Hiroki Hayashi, Saeesh R Mangaonkar, Tsuyoshi Mita
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Trans-Selective Carboxylative Cyclization of 1,6-Dienes Using the CO2 Radical Anion
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.
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.