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Updated: May 13, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis
Fenghai Guo1, Michael D Clift, Regan J Thomson
1Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, Illinois 60208, USA.
Abstract:
The oxidative coupling of enolates, enol silanes, and enamines provides a direct method for the construction of useful 1,4-dicarbonyl synthons. Despite being first reported in 1935, with subsequent important advances beginning in the 1970's, the development of this powerful reaction into a reliable methodology was somewhat limited. In recent years, there have been a number of reports from several research groups demonstrating advances in several neglected areas of oxidative coupling. This microreview summarizes these new advances in methodology and provides an overview of recent natural product syntheses that showcase the power of these transformations.
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