Issue 31, 2025

Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of trisubstituted pyrrole and chiral dihydropyrrole-3-carbaldehydes

Abstract

A unique approach has been developed to synthesize trisubstituted 1H-pyrrole-3-carbaldehydes using 4-methyl thiazolium salts, α,β-unsaturated aldehydes, and organocatalysts via a domino 1,3-dipolar cycloaddition/ring-opening/C–S and C–N bond cleavage reaction sequence. This methodology has been successfully extended for the asymmetric synthesis of enantioenriched trisubstituted-4,5-dihydro-1H-pyrrole-3-carbaldehydes employing chiral amine organocatalysts with high efficiency (up to 98% ee, >20 : 1 d.r.).

Graphical abstract: Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of trisubstituted pyrrole and chiral dihydropyrrole-3-carbaldehydes

Supplementary files

Article information

Article type
Communication
Submitted
24 Dec 2024
Accepted
14 Mar 2025
First published
15 Mar 2025

Chem. Commun., 2025,61, 5806-5809

Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of trisubstituted pyrrole and chiral dihydropyrrole-3-carbaldehydes

S. Pandidurai, M. Chinababu and G. Sekar, Chem. Commun., 2025, 61, 5806 DOI: 10.1039/D4CC06706A

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