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Updated: Jan 20, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Direct Ether Synthesis Utilizing the Carbonyl Umpolung Reaction
Isao Mizota1, Miyuki Hotta1, Ayaki Yamamoto1
1Department of Applied Chemistry, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
Abstract:
A direct ether synthesis was achieved by treating an α-ketoamide with a Grignard reagent, providing a simple one-step procedure compared with that of conventional ether-forming methods. This carbonyl umpolung-based O-alkylation proceeds smoothly to afford α-alkoxyamides in good yields. Furthermore, a tandem O-alkylation/aldol reaction with aldehydes was also developed to afford the desired aldol products with high diastereoselectivity.
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