Copper-Mediated Single-Electron Approach to Indoline Amination: Scope, Mechanism, and Total Synthesis of Asperazine A
作者:James B. Shaum、Andrei Nikolaev、Helena C. Steffens、Luis Gonzalez、Shamon Walker、Andrey V. Samoshin、Gabrielle Hammersley、Ellia H. La、Javier Read de Alaniz
DOI:10.1021/acs.joc.2c00923
日期:2022.8.5
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
带有 C3-N 键的吡咯并吲哚啉构成了许多具有生物活性的天然产物的核心,但许多合成它们的方法受到产品的空间位阻或电子学的限制。我们报告了一种基于单电子的方法来合成这种支架,并展示了高产胺化,无论电子或空间需求如何。该转化使用铜丝和异丙醇来促进反应。包括这种非均相铜催化方法获得吡咯并二氢吲哚、二酮哌嗪、呋喃二氢吲哚和 (+)-阿哌嗪的广泛合成效用,以及提供对这一新工艺机制的深入了解的实验。