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Updated: May 20, 2025

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Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of trisubstituted pyrrole and chiral
Solai Pandidurai1, Maddala Chinababu1, Govindasamy Sekar1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, India. gsekar@iitm.ac.in.
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.).
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