ArticleNature communications2024
Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination.
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 8 papers.
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Who cites it
8 citing papers in PubMed.
- Stereoselective synthesis of E-shaped double helicene analogues via organocatalytic intermolecular cycloaddition.Nature communications · 2026Article
- Enantioselective construction of polychiral helical compounds via dynamic kinetic resolution.Nature communications · 2026Article
- Catalytic enantioselective synthesis of azahelicenes via cascade Pictet-Spengler reaction and dehydrogenative aromatization.Nature communications · 2026Article
- Screwing the helical chirality through terminalBeilstein journal of organic chemistry · 2026Article
- Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization.Nature communications · 2025Article
- Control of Dynamic Chirality in Donor-Acceptor Fluorophores.Angewandte Chemie (International ed. in English) · 2025Article
- Organocatalytic enantioselective synthesis of double S-shaped quadruple helicene-like molecules.Nature communications · 2025Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
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Authors and funding
8 authors.
Funding
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Abstract
Catalytic asymmetric synthesis of helically chiral molecules has remained an outstanding challenge and witnessed fairly limited progress in the past decades. Current methods to construct such compounds almost entirely rely on catalytic enantiocontrolled fused-ring system extension. Herein, we report a direct terminal peri-functionalization strategy, which allows for efficient assembling of 1,12-disubstituted [4]carbohelicenes via an organocatalyzed enantioselective amination reaction of 2-hydroxybenzo[c]phenanthrene derivates with diazodicarboxamides. The key feature of this approach is that the stereochemical information of the catalyst could be transferred into not only the helix sense but also the remote C-N axial chirality of the products, thus enabling the synthesis of [4]- and [5]helicenes with both structural diversity and stereochemical complexity in good efficiency and excellent enantiocontrol. Besides, the large-scale preparations and representative transformations of the helical products further demonstrate the practicality of this protocol. Moreover, DFT calculations reveal that both the hydrogen bonds and the C-H---π interactions between the substrates and catalyst contribute to the ideal stereochemical control.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.