Copper-Mediated Single-Electron Approach to Indoline Amination: Scope, Mechanism, and Total Synthesis of Asperazine A
Copper-Mediated Single-Electron Approach to Indoline Amination: Scope, Mechanism, and Total Synthesis of Asperazine A
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DOI：
10.1021/acs.joc.2c00923
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发表时间：
2022-07-25
影响因子：
3.6
通讯作者：
de Alaniz，Javier Read
中科院分区：
文献类型：
--
作者：
Shaum，James B.;Nikolaev，Andrei;de Alaniz，Javier Read
具有C3-N键的吡咯并吲哚啉是许多具有生物活性的天然产物的核心，但是许多合成它们的方法受到产物的空间或电子学的限制。我们报告了一个单一的电子为基础的方法，这种支架的合成，并证明高产胺化，无论电子或空间的需求。转化采用铜丝和异丙醇促进反应。广泛的合成效用，这种异质铜催化的方法，以获得吡咯并吲哚啉，二酮哌嗪，呋喃并吲哚啉，（+）-阿斯帕嗪包括，沿着实验，以提供深入了解这一新的过程的机制。
Pyrroloindolines bearing a C3–N linkage comprise the core of many biologically active natural products, but many methods toward their synthesis are limited by the sterics or electronics of the product. We report a single electron-based approach for the synthesis of this scaffold and demonstrate high-yielding aminations, regardless of electronic or steric demands. The transformation uses copper wire and isopropanol to promote the reaction. The broad synthetic utility of this heterogeneous copper-catalyzed approach to access pyrroloindolines, diketopiperazine, furoindoline, and (+)-asperazine is included, along with experiments to provide insight into the mechanism of this new process.