ArticleJournal of the American Chemical Society2016
Metal-Templated Design: Enantioselective Hydrogen-Bond-Driven Catalysis Requiring Only Parts-per-Million Catalyst Loading.
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 15 papers.
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Who cites it
15 citing papers in PubMed.
- Stereogenic-at-Metal Ir(III) Complexes as Platforms for the Construction of Asymmetric Bimetallic Complexes.Inorganic chemistry · 2025Article
- Chiral-at-metal catalysts: history, terminology, design, synthesis, and applications.Chemical Society reviews · 2025Review
- Ringing the Changes: Effects of Heterocyclic Ring Size on Stereoselectivity in [(ηMolecules (Basel, Switzerland) · 2024Article
- Enantioselective Paternò-Büchi Reactions: Strategic Application of a Triplet Rebound Mechanism for Asymmetric Photocatalysis.Journal of the American Chemical Society · 2024Article
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- A Degenerate Metal-Templated Catalytic System with Redundant Functional Groups for the Asymmetric Aldol Reaction.The Journal of organic chemistry · 2022Article
- Recent Development of Bis-Cyclometalated Chiral-at-Iridium and Rhodium Complexes for Asymmetric Catalysis.ACS organic & inorganic Au · 2022Review
- Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines.Journal of the American Chemical Society · 2021Article
- Recent Developments in Enantioselective Transition Metal Catalysis Featuring Attractive Noncovalent Interactions between Ligand and Substrate.ACS catalysis · 2020Review
- Transition State Force Field for the Asymmetric Redox-Relay Heck Reaction.Journal of the American Chemical Society · 2020Article
- Organocatalytic Michael Addition to (D)-Mannitol-Derived Enantiopure Nitroalkenes: A Valuable Strategy for the Synthesis of Densely Functionalized Chiral Molecules.Molecules (Basel, Switzerland) · 2019Article
- Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction.Nature chemistry · 2018Article
- Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.Nature protocols · 2018Article
- Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer.Journal of the American Chemical Society · 2017Article
- CHScientific reports · 2017Article
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12 authors.
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Abstract
Based on a metal-templated approach using a rigid and globular structural scaffold in the form of a bis-cyclometalated octahedral iridium complex, an exceptionally active hydrogen-bond-mediated asymmetric catalyst was developed and its mode of action investigated by crystallography, NMR, computation, kinetic experiments, comparison with a rhodium congener, and reactions in the presence of competing H-bond donors and acceptors. Relying exclusively on weak forces, the enantioselective conjugate reduction of nitroalkenes can be executed at catalyst loadings as low as 0.004 mol% (40 ppm), representing turnover numbers of up to 20 250. A rate acceleration by the catalyst of 2.5 × 10(5) was determined. The origin of the catalysis is traced to an effective stabilization of developing charges in the transition state by carefully orchestrated hydrogen-bonding and van der Waals interactions between catalyst and substrates. This study demonstrates that the proficiency of asymmetric catalysis merely driven by hydrogen-bonding and van der Waals interactions can rival traditional activation through direct transition metal coordination of the substrate.
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