Copper-Catalyzed Asymmetric Yne-Allylic Substitution Using Electron-Rich Arenes,ACS Catalysis

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Copper-Catalyzed Asymmetric Yne-Allylic Substitution Using Electron-Rich Arenes
ACS Catalysis ( IF 11.3 ) Pub Date : 2024-02-07 , DOI: 10.1021/acscatal.3c06146
Defu Luo ₁ , Shengtong Niu ₁ , Fan Gong ₁ , Chao Xu ₁ , Shouang Lan ₁ , Jinggong Liu ₂ , Shuang Yang ₁ , Xinqiang Fang ₁

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Remote stereocontrol in transition-metal catalysis is a challenging but interesting research topic. In this work, we achieved copper-catalyzed asymmetric yne-allylic substitution using electron-rich arenes and acyclic carbonates through remote enantioselectivity control. The reaction delivers a variety of enantioenriched products that contain a diverse set of valuable moieties, such as conjugated enynes, indoles, indolizines, allenes, and dihydrofurans, which are widely used in organic synthesis and act as key units in bioactive molecules and natural products. The synthetic value of this protocol has been demonstrated in a series of further transformations, and mechanistic studies have been conducted to gain more insight into the reaction.

中文翻译：

使用富电子芳烃的铜催化不对称炔烯丙基取代

过渡金属催化中的远程立体控制是一个具有挑战性但有趣的研究课题。在这项工作中，我们通过远程对映选择性控制，使用富电子芳烃和无环碳酸酯实现了铜催化的不对称炔烯丙基取代。该反应产生各种对映体富集的产物，其中含有多种有价值的部分，例如共轭烯炔、吲哚、中氮茚、丙二烯和二氢呋喃，它们广泛用于有机合成，是生物活性分子和天然产物的关键单元。该方案的合成价值已在一系列进一步的转化中得到证明，并进行了机理研究以更深入地了解该反应。

更新日期：2024-02-07

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