Construction of 3‐Azabicyclo[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines via Tandem Michael Addition and Copper‐Mediated Oxidative Carbanion Cyclization,Chinese Journal of Chemistry

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Construction of 3‐Azabicyclo[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines via Tandem Michael Addition and Copper‐Mediated Oxidative Carbanion Cyclization
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-10-26 , DOI: 10.1002/cjoc.202000405
Hui Xu ₁ , Teng Han ₁ , Xiaoyan Luo ₁ , Wei‐Ping Deng ₁

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A facile synthetic method for the construction of 3‐azabicyclo[3.1.0]hexane in the presence of copper catalyst system was developed. The reaction proceeds through Michael addition of allylamines with allenes followed by copper‐mediated intramolecular oxidative carbanion 5‐exo‐trig radical cyclization, affording potential biologically active 3‐azabicyclo[3.1.0]hexane derivatives in moderate to high yields (42%—85%).

中文翻译：

通过串联迈克尔加成反应和铜介导的氧化碳环化反应，通过丙二烯与烯丙胺的反应构建3-氮杂双环[3.1.0]己烷主链

开发了一种在铜催化剂体系存在下构造3-氮杂双环[3.1.0]己烷的简便合成方法。该反应通过将烯丙胺与烯丙基进行迈克尔加成反应，然后进行铜介导的分子内氧化碳负离子5-外-trig自由基环化，以中等至高产率提供潜在的具有生物活性的3-氮杂双环[3.1.0]己烷衍生物（42％-85 ％）。

更新日期：2020-10-26

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