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Issue 30, 2020
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Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals

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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.

Graphical abstract: Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals

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Article information


Submitted
16 Apr 2020
Accepted
07 Jul 2020
First published
07 Jul 2020

Org. Biomol. Chem., 2020,18, 5816-5821
Article type
Communication

Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals

A. Przydacz, M. Dyguda, A. Topolska, A. Skrzyńska, C. Xu, Y. Chen and Ł. Albrecht, Org. Biomol. Chem., 2020, 18, 5816
DOI: 10.1039/D0OB00788A

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