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Updated: Mar 12, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
CuCl-Promoted β-Acylation of Cyclopropanols with Thioesters
Savva Ponomarev1, Sandra W Papińska1, Michael Stier2
1Institute of Organic Chemistry, Faculty of Science, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Abstract:
CuCl-induced cyclopropyl alcohol ring-opening followed by β-acylation with thioester is reported. Cyclopropanols and thioesters with various substitution patterns were successfully subjected to the reaction, and a series of 1,4-dicarbonyl compounds were synthesized. The mechanistic investigation revealed the involvement of Cu(I)-homoenolate, which reacts with the thioester via oxidative addition. Both experimental and computational evidence were found. Operational simplicity, high chemo- and regioselectivity, and good to excellent yields are the core features of the presented approach.
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