Selective Amination Reactions of 伪-Nitro Aryl and Heteroaryl Enoates

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• 作者：Stefania Fioravanti ; Lucio Pellacani ; Maria Cecilia Vergari
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：78
• 期：16
• 页码：8203-8207
• 全文大小：284K
• 年卷期：v.78,no.16(August 16, 2013)
• ISSN：1520-6904

文摘

Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various 伪-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-尾-amino 伪-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for 伪-nitro alkyl enoates or 尾-nitro allylic alcohols.