Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes

Gianpiero Cera; Davide Balestri; Margherita Bazzoni; Luciano Marchiò; Andrea Secchi; Arturo Arduini

doi:10.1039/D0OB01319F

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Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes†

Gianpiero Cera,

*^a Davide Balestri,

^a Margherita Bazzoni,

^a Luciano Marchiò,^a Andrea Secchi

*^a and Arturo Arduini

*^a

Author affiliations

* Corresponding authors

^a Università di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy
E-mail: gianpiero.cera@unipr.it, andrea.secchi@unipr.it, arturo.arduini@unipr.it

Abstract

We describe the application of a novel family of trisulfonamide (TSA) calix[6]arenes in general acid catalysis. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles to nitroalkene derivatives. The transformation occurs at a low catalyst loading of 5 mol%, allowing for the synthesis of nitroalkanes with good yields and functional group tolerance.

This article is part of the themed collection: Catalysis & biocatalysis in OBC

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DOI: https://doi.org/10.1039/D0OB01319F
Article type: Communication
Submitted: 27 Jun 2020
Accepted: 15 Jul 2020
First published: 24 Jul 2020

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Org. Biomol. Chem., 2020,18, 6241-6246

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Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes

G. Cera, D. Balestri, M. Bazzoni, L. Marchiò, A. Secchi and A. Arduini, Org. Biomol. Chem., 2020, 18, 6241 DOI: 10.1039/D0OB01319F

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Organic & Biomolecular Chemistry

Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes†

Abstract

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Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes

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