Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation?
Organic & Biomolecular Chemistry Pub Date: 2022-04-19 DOI: 10.1039/D2OB00536K
Abstract
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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