ArticleNature communications2023
Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination.
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 16 papers.
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Who cites it
16 citing papers in PubMed.
- Chiral Brønsted acid-catalyzed kinetic resolution of radical additions.Nature communications · 2026Article
- Asymmetric synthesis of planar-chiral metacyclophanesChemical science · 2026Article
- Catalytic enantioselective synthesis of azahelicenes via cascade Pictet-Spengler reaction and dehydrogenative aromatization.Nature communications · 2026Article
- Construction of remote dual stereocenters by electrochemical cobalt-catalyzed enantioselective desymmetrization.Nature communications · 2026Article
- Isothiourea-Catalysed Acylative Kinetic and Dynamic Kinetic Resolution of Planar Chiral Paracyclophanols.Angewandte Chemie (International ed. in English) · 2025Article
- Stereocontrolled Construction of Multi-Chiral [2.2]Paracyclophanes via Cobaltaphotoredox Dual Catalysis.ACS catalysis · 2025Article
- Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition.Nature communications · 2025Article
- Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization.Nature communications · 2025Article
- Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules.Beilstein journal of organic chemistry · 2025Review
- Azocarboxamide-enabled enantioselective regiodivergent unsymmetrical 1,2-diaminations.Nature communications · 2024Article
- Synthesis of Novel Planar-Chiral Charge-CompensatedMolecules (Basel, Switzerland) · 2024Article
- Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Catalytic asymmetric synthesis of planar-chiral dianthranilides via (Dynamic) kinetic resolution.Nature communications · 2024Article
- Rhodium(II)-Catalyzed Asymmetric Cyclopropanation and Desymmetrization of [2.2]Paracyclophanes.ACS catalysis · 2024Article
- Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes.Nature communications · 2024Article
- Asymmetric synthesis of P-stereogenic phosphindane oxides via kinetic resolution and their biological activity.Nature communications · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
Planar chiral [2.2]paracyclophane derivatives are a type of structurally intriguing and practically useful chiral molecules, which have found a range of important applications in the field of asymmetric catalysis and material science. However, access to enantioenriched [2.2]paracyclophanes represents a longstanding challenge in organic synthesis due to their unique structures, which are still highly dependent on the chiral chromatography separation technique and classical chemical resolution strategy to date. In this work, we report on an efficient and versatile kinetic resolution protocol for various substituted amido[2.2]paracyclophanes, including those with pseudo-geminal, pseudo-ortho, pseudo-meta and pseudo-para disubstitutions, using chiral phosphoric acid (CPA)-catalyzed asymmetric amination reaction, which was also applicable to the enantioselective desymmetrization of an achiral diamido[2.2]paracyclophane. Detailed experimental studies shed light on a new reaction mechanism for the electrophilic aromatic C-H amination, which proceeded through sequential triazane formation and N[1,5]-rearrangement. The facile large-scale kinetic resolution reaction and diverse derivatizations of both the recovered chiral starting materials and the C-H amination products showcased the potential of this method.
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