ArticleChemical science2015
Selective acceleration of disfavored enolate addition reactions by anion-π interactions.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- Electric-Field Catalysis on Carbon Nanotubes in Electromicrofluidic Reactors: Monoterpene Cyclizations.Angewandte Chemie (International ed. in English) · 2025Article
- Electric field-assisted anion-π catalysis on carbon nanotubes in electrochemical microfluidic devices.Science advances · 2023Article
- The Origin of Anion-π Autocatalysis.JACS Au · 2023Article
- Anion-π catalysis on carbon allotropes.Beilstein journal of organic chemistry · 2023Review
- Decoded fingerprints of hyperresponsive, expanding product space: polyether cascade cyclizations as tools to elucidate supramolecular catalysis.Chemical science · 2022Article
- Anion-π Catalysis Enabled by the Mechanical Bond.Angewandte Chemie (International ed. in English) · 2022Article
- Covalent and Non-covalent Noble Gas Bonding Interactions in XeFFrontiers in chemistry · 2020Article
- Remote Control of Anion-π Catalysis on Fullerene-Centered Catalytic Triads.Angewandte Chemie (International ed. in English) · 2018Article
- Catalysis with Pnictogen, Chalcogen, and Halogen Bonds.Angewandte Chemie (International ed. in English) · 2018Article
- Review
- Anion-π Enzymes.ACS central science · 2016Article
- Core-Substituted Naphthalenediimides: LUMO Levels Revisited, in Comparison with Preylenediimides with Sulfur Redox Switches in the Core.ChemistryOpen · 2016Article
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Authors and funding
4 authors.
Funding
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Abstract
In chemistry and biology, cation-π interactions contribute significantly to many important transformations. In sharp contrast, reactions accomplished with support from the complementary anion-π interactions are essentially unknown. In this report, we show that anion-π interactions can determine the selectivity of the enolate chemistry of malonate half thioesters. Their addition to enolate acceptors is central in natural product biosynthesis but fails without enzymes because non-productive decarboxylation dominates. The newly designed and synthesized anion-π tweezers invert this selectivity by accelerating the disfavored and decelerating the favored process. The discrimination of anionic tautomers of different planarization and charge delocalization on π-acidic surfaces is expected to account for this intriguing "tortoise-and-hare catalysis." Almost exponentially increasing selectivity with increasing π acidity of the catalyst supports that contributions from anion-π interactions are decisive.
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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.