Related Experiment Video
Updated: Mar 21, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Cu-Catalyzed Stereoselective γ-Alkylation of Enones
Xiaohong Chen1, Xiaoguang Liu1, Justin T Mohr1
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
Abstract:
A general regio- and stereoselective γ-C-C bond formation is achieved using α-halocarbonyl compounds and dienol ethers via Cu(II) catalysis. This method constitutes a novel approach to the challenging 1,6-dioxygenation motif. A range of γ-substituted enones, including many bearing all-carbon quaternary centers, are available through a simple protocol under mild reaction conditions with superb functional group compatibility. Excellent stereoinduction is observed providing controlled access to challenging stereochemical arrays.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Related Concept Videos
α-Alkylation of Ketones via Enolate Ions
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Stereochemical Effects of Enolization
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation