ArticleNature communications2024
Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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Who cites it
5 citing papers in PubMed.
- Copper-catalysed dynamic kinetic (4+1) cyclization of 1,3-enynes for atroposelective arylpyrrole synthesis.Nature communications · 2026Article
- Vinyl-aza-[3]cumulene intermediates induced polymerization for accessing E-dienyl poly(sulfonylamidines) towards pH-responsive drug delivery.Nature communications · 2025Article
- Chiral Copper Catalysis in Enantioselective Domino Reactions.Molecules (Basel, Switzerland) · 2025Review
- Azapeptide Atropisomers From Late-StageThe Journal of organic chemistry · 2025Article
- Copper-catalyzed yne-allylic substitutions: concept and recent developments.Beilstein journal of organic chemistry · 2024Review
Corrections and comments
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Authors and funding
11 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The construction of atropisomers with 1,2-diaxes, while maintaining high enantiocontrol, presents a significant challenge due to the dynamic nature of steric hindrance at ortho-aryl substituents. Although various catalytic asymmetric methods have been developed for accessing axially chiral arylpyrroles, the synthesis of axially chiral arylpyrroles with 1,2-diaxes in a catalytic asymmetric manner has remained rare. Herein, the authors report the synthesis of diverse axially chiral arylpyrroles with 1,2-diaxes, and C-C and C-N axes through copper-catalysed asymmetirc [4 + 1] annulation of yne-allylic esters with arylamines via a remote stereocontrol strategy. This approach provides facile access to a broad range of heterobiaryl atropisomers (67 examples) in excellent enantioselectivities, each bearing one or two C-C/C-N axes, demonstrating its versatility and efficiency. The utility of this methodology is further highlighted by the transformation of the product into chiral phosphine ligand, and chiral thioureas for the use in asymmetric catalysis.
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Registered trials
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