ArticleNature communications2023
Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Asymmetric C2-functionalization of indoles via visible-light-promoted three-component reaction.Molecular diversity · 2026Article
- A unified and desymmetric approach to axially chiral atropisomers.Nature communications · 2026Article
- Catalytic asymmetric formal nucleophilic C2-substitution of indoles via C2-umpolung toward 2,3'-bisindole atropisomers.Nature communications · 2026Article
- Copper-catalysed dynamic kinetic (4+1) cyclization of 1,3-enynes for atroposelective arylpyrrole synthesis.Nature communications · 2026Article
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides.Nature communications · 2025Article
- Construction of axially chiral molecules enabled by photoinduced enantioselective reactions.Chemical science · 2024Review
- Catalytic Asymmetric Construction of α,α-Diaryl Aldehydes via Oxo-Hydroarylation of Terminal Alkynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Copper-catalyzed atroposelective synthesis of C-O axially chiral compounds enabled by chiral 1,8-naphthyridine based ligands.Chemical science · 2024Article
- Atroposelective Synthesis of Axially Chiral Naphthylpyrroles by a Catalytic Asymmetric 1,3-Dipolar Cycloaddition/Aromatization Sequence.Organic letters · 2024Article
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Authors and funding
6 authors.
Funding
Abstract
The C-N axially chiral N-arylpyrrole motifs are privileged scaffolds in numerous biologically active molecules and natural products, as well as in chiral ligands/catalysts. Asymmetric synthesis of N-arylpyrroles, however, is still challenging, and the simultaneous creation of contiguous C-N axial and central chirality remains unknown. Herein, a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis has been developed. The key transformation is a one-pot, three-component oxo-diarylation reaction, which simultaneously creates a C-N axial chirality and a central quaternary stereogenic center. A broad range of unactivated alkynes were readily employed as a reaction partner in this transformation, and the N-arylpyrrole products are obtained in good yields, with excellent enantioselectivities and very good diastereoselectivities. Notably, the N-arylpyrrole skeletons represent interesting structural motifs that could be used as chiral ligands and catalysts in asymmetric catalysis.
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