ArticleJournal of the American Chemical Society2023
Amino Acid-Derived Ionic Chiral Catalysts Enable Desymmetrizing Cross-Coupling to Remote Acyclic Quaternary Stereocenters.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 34 citations in OpenAlex.
- Remote desymmetrization of tetraoxacalix[2]arene[2]triazines enables the asymmetric synthesis of inherently chiral heteracalix[4]aromatics.Chemical science · 2026Article
- Optimization of a Resolution Process Allowing Access to Both Enantiomers of the Versatile Chiral Phosphine Ligand sSPhos on Scale.Organic process research & development · 2026Article
- Chiral LiPS-LiTFSI dimers enabling biomimetic electrocatalysis in lithium||sulfur batteries.Nature communications · 2026Article
- Asymmetric Desymmetrizing Sulfonylation of Diarylmethanes via Peptidyl-Cu(I)-Catalysis with Remote Stereocontrol.Journal of the American Chemical Society · 2026Article
- Spatial Assembly of Mechanically Planar Chiral Rotaxanes on Rationally Designed Cavitands.Angewandte Chemie (International ed. in English) · 2025Article
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki-Miyaura cross-coupling.Nature communications · 2025Article
- Palladium-catalyzed enantioselective β-hydride elimination for the construction of remote stereocenters.Nature communications · 2025Article
- Article
- Catalytic asymmetric C-N cross-coupling towards boron-stereogenic 3-amino-BODIPYs.Nature communications · 2025Article
- Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions.Beilstein journal of organic chemistry · 2025Article
- sSPhos: A General Ligand for Enantioselective Arylative Phenol Dearomatization via Electrostatically-Directed Palladium Catalysis.Journal of the American Chemical Society · 2023Article
- An Asymmetric Aromatic Finkelstein Reaction: A Platform for Remote Diarylmethane Desymmetrization.Journal of the American Chemical Society · 2023Article
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Synthetic application of asymmetric catalysis relies on strategic alignment of bond construction to creation of chirality of a target molecule. Remote desymmetrization offers distinctive advantages of spatial decoupling of catalytic transformation and generation of a stereogenic element. However, such spatial separation presents substantial difficulties for the chiral catalyst to discriminate distant enantiotopic sites through a reaction three or more bonds away from a prochirality center. Here, we report a strategy that establishes acyclic quaternary carbon stereocenters through cross-coupling reactions at distal positions of aryl substituents. The new class of amino acid-derived ionic chiral catalysts enables desymmetrizing (enantiotopic-group-selective) Suzuki-Miyaura reaction, Sonogashira reaction, and Buchwald-Hartwig amination between diverse diarylmethane scaffolds and aryl, alkynyl, and amino coupling partners, providing rapid access to enantioenriched molecules that project substituents to widely spaced positions in the three-dimensional space. Experimental and computational investigations reveal electrostatic steering of substrates by the C-terminus of chiral ligands through ionic interactions. Cooperative ion-dipole interactions between the catalyst's amide group and potassium cation aid in the preorganization that transmits asymmetry to the product. This study demonstrates that it is practical to achieve precise long-range stereocontrol through engineering the spatial arrangements of the ionic catalysts' substrate-recognizing groups and metal centers.
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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.