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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
Organocatalytic modular synthesis of 2-functionalized 2,5-dihydrofurans from γ-hydroxy enals
Tie Lei1, Jun Tan1, Yifei Zhang1
1School of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, China. madk@ccmu.edu.cn.
Abstract:
A convenient and modular method for the preparation of diverse 2-O/N/C-functionalized 2,5-dihydrofurans has been developed starting from readily available γ-hydroxy enals via organocatalysis. This reaction features broad substrate scope, excellent functional group tolerance, high efficiency, and green properties, with high atom economy and water as the sole byproduct. Its potential applications in organic synthesis and drug discovery are demonstrated through late-stage functionalization of natural products and drugs, as well as synthetic transformations. Detailed mechanistic studies provide valuable insights into the reaction pathway.
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