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Updated: Dec 14, 2025
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals
Artur Przydacz1, Mateusz Dyguda, Aleksandra Topolska
1Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland. lukasz.albrecht@p.lodz.pl.
Abstract:
The manuscript describes a straightforward functionalization of 2-alkyl-3-furfurals via simple aminocatalytic conjugate addition. The reaction proceeds through the formation of dearomatized dienamine-like intermediate that undergoes 1,6-addition to 4-alkylidene-2,6-dialkylcyclohexa-2,5-dienones. This process can be described as doubly rearomative as it proceeds with the re-formation of both furan and phenyl aromatic moieties. Target products have been obtained in a highly stereoselective manner, providing an interesting example of 2-alkyl-3-furfural functionalization via doubly vinylogous Michael addition. The mechanism of the reaction has been studied by means of computational methods.
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