ArticleJournal of the American Chemical Society2016
On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed.
- Recent Progress in Catalytic Asymmetric Pictet-Spengler Reaction to Construct 1,1-Disubstituted Scaffolds.Synthesis · 2026Article
- Catalytic Enantioselective Synthesis of 1,1-Disubstituted Isochromans.Journal of the American Chemical Society · 2026Article
- An anion-binding approach to enantioselective photoredox catalysis.Science (New York, N.Y.) · 2025Article
- Article
- The impact of supramolecular self-association of organocatalysts on catalytic performance.Nature reviews. Chemistry · 2025Review
- Harnessing Noncovalent π‑Type Interactions in Thiourea-Chloride Supramolecular Complexes: Toward the Asymmetric Dearomatization of Diazaheterocycles.ACS catalysis · 2025Article
- Toward Chiral Recognition by Design: Uncovering the Self-Enantioresolving Properties of Chiral Amine Derivatives.Journal of the American Chemical Society · 2025Article
- Carbazole Framework as Functional Scaffold for the Design of Synthetic Receptors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Highly enantioselective synthesis of both tetrahydroquinoxalines and dihydroquinoxalinonesChemical science · 2023Article
- Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet-Spengler Reaction and the Development of a Stereodivergent Variant.ACS catalysis · 2023Article
- Turning Enantiomeric Relationships into Diastereomeric Ones: Self-Resolving α-Ureidophosphonates and Their Organocatalytic Enantioselective Synthesis.Journal of the American Chemical Society · 2022Article
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
- Relevance of the Cation in Anion Binding of a Triazole Host: An Analysis by Electrophoretic Nuclear Magnetic Resonance.The journal of physical chemistry. B · 2022Article
- Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.Journal of the American Chemical Society · 2022Review
- Kinetic Analysis of a Cysteine-Derived Thiyl-Catalyzed Asymmetric Vinylcyclopropane Cycloaddition Reflects Numerous Attractive Noncovalent Interactions.Journal of the American Chemical Society · 2021Article
- Enantioselective Synthesis of α-Aryl-βAngewandte Chemie (International ed. in English) · 2021Article
- N,N-Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion-Binding Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
- Halides as versatile anions in asymmetric anion-binding organocatalysis.Beilstein journal of organic chemistry · 2021Review
- Insight into the Folding and Cooperative Multi-Recognition Mechanism in Supramolecular Anion-Binding Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques.International journal of molecular sciences · 2020Review
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Chiral, neutral H-bond donors have found widespread use as catalysts in enantioselective reactions involving ion-pair intermediates. Herein, a systematic mechanistic study of a prototypical anion-binding reaction, the thiourea-catalyzed enantioselective alkylation of α-chloroethers, is detailed. This study reveals that the catalyst resting state is an inactive dimeric aggregate that must dissociate and then reassemble to form a 2:1 catalyst-substrate complex in the rate-determining transition structure. Insight into this mode of catalyst cooperativity sheds light on the practical limitations that have plagued many of the H-bond donor-catalyzed reactions developed to date and suggests design strategies for new, highly efficient catalyst structures.
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