Immobilized L-aspartic acid beta-methyl ester (Fmoc-Asp(OMe)-OH) was reacted with 4-nitrobenzenesulfonyl chloride, followed by alkylation with various α-haloketones. The resulting intermediates were treated with potassium trimethylsilanolate, which yielded tetrasubstituted pyrroles after a one-step transformation consisting of sequential C-arylation, aldol condensation and spontaneous aromatization. The discovered synthetic strategy enables fast and simple access to pentasubstituted and functionalized pyrroles from a number of readily available starting materials.

Department of Organic Chemistry Faculty of Science Palacký University 17 Listopadu 12 77146 Olomouc Czech Republic

Institute of Molecular and Translational Medicine Faculty of Medicine and Dentistry Palacký University Hněvotínská 5 77900 Olomouc Czech Republic

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References provided by Crossref.org

Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino-Acid-Based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides

Synthesis of Polysubstituted Pyridines and Pyrazines via Truce-Smiles Rearrangement of Amino Acid-Based 4-Nitrobenzenesulfonamides