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Updated: Sep 9, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Iodine-Promoted Ring-Opening α,β-Difunctionalization of Cyclopropanols with Enaminones: A Selective Route to
Jun-Long Zhan1, Jiang-Shan Wei1, Sheng-Ling Yuan1
1Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs. College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China.
Abstract:
In this work, we report a novel I2-mediated ring-opening α,β-difunctionalization of cyclopropyl alcohols with enaminones for the first time. The selective [3 + 2] annulation instead of [3 + 3] annulation under metal-free conditions enables a straightforward and efficient synthesis of structurally important 2,4-diacylpyrroles. Notably, this methodology dispenses with metal catalysts, proceeds under mild reaction conditions, and features not only simple operation but also suitability for gram-scale preparation and late-stage functionalization of complex bioactive molecules.
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