ArticleNature communications2025
Organocatalytic enantioselective synthesis of double S-shaped quadruple helicene-like molecules.
Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 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
- Skeletal rearrangement of [4]helicenes under acidic conditions: dynamic chirality and improved properties by subsequent peripheral editing.Chemical science · 2026Article
- Catalytic enantioselective synthesis of azahelicenes via cascade Pictet-Spengler reaction and dehydrogenative aromatization.Nature communications · 2026Article
- Two-photon Excitation of Bright Diaza[4]Helicenes for Isotropic and Circularly Polarized Emission.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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Authors and funding
8 authors.
Funding
Abstract
Helicene-shaped molecules are compelling chemical structures with unique twisted helical chirality and remarkable properties. Although progress occurs in the catalytic asymmetric synthesis of helicene (-like) molecules, the enantioselective synthesis of multiple helicenes, especially four or higher helicity, is still challenging and has yet to be achieved. Herein, we report an organocatalytic [4 + 2] cycloadditions to achieve double S-shaped quadruple helicene-like molecules with high enantioselectivity (up to 96% e.e.). The enantioselective synthesis of (P,P,P,P) and (M,M,M,M) configurational quadruple helical molecules can be achieved by modulating the structure of the catalyst. Density functional theory (DFT) calculations show that the reaction involves the formation of a duplex vinylidene ortho-quinone methide (VQM) intermediate and two successive cycloaddition reactions. Configurational stability studies elucidate the isomerization process between the isomers. In addition, the structural features and optical properties of the quadruple helicene-like molecules were investigated to explore their potential applications.
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