Issue 11, 2025

Supramolecular catalysis in the dearomative Michael addition involving nitro-group-activated benzofurans

Abstract

In this manuscript, the application of supramolecular catalysis utilizing the combination of a cinchona-alkaloid-derived squaramide and an acidic co-catalyst in the vinylogous, dearomative Michael addition is described. The appropriate selection of reaction promotors allowing for the self-assembly of a well-defined transition state resulted in the formation of biologically relevant heterocycles bearing three contiguous stereocenters with high stereoselectivity. The synthetic potential of the methodology was confirmed in selected post-functionalizations including removal of the nitro group with concomitant aromatization and the thia-Michael reaction. Furthermore, the mechanism of the reaction has been studied using DFT calculations indicating the importance of supramolecular interactions for the reaction outcome.

Graphical abstract: Supramolecular catalysis in the dearomative Michael addition involving nitro-group-activated benzofurans

Supplementary files

Article information

Article type
Research Article
Submitted
06 Jan 2025
Accepted
15 Mar 2025
First published
20 Mar 2025

Org. Chem. Front., 2025,12, 3324-3329

Supramolecular catalysis in the dearomative Michael addition involving nitro-group-activated benzofurans

A. Topolska, A. Przydacz, A. Skrzyńska and Ł. Albrecht, Org. Chem. Front., 2025, 12, 3324 DOI: 10.1039/D5QO00035A

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