ArticleAngewandte Chemie (International ed. in English)2021
London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey-Bakshi-Shibata Reduction.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Assessing Benzene Dimer Interactions in Solution With a Molecular Balance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- London Dispersion in Confined Chiral Ion-Pair Asymmetric Catalysis: From Background Interaction to Design Principle.Accounts of chemical research · 2026Article
- Intermolecular Interactions of Linear Alkane (ACS omega · 2026Article
- London Dispersion FavorsThe Journal of organic chemistry · 2026Review
- Dispersion-Enhanced Nitrogen-Centered Photocatalysis of the Direct Hydrogen Atom Transfer.Angewandte Chemie (International ed. in English) · 2026Article
- Stereoselective Generalizations over Diverse Sets of Chiral Acids Enabled by Buried Volume.Journal of the American Chemical Society · 2026Article
- Attractive Noncovalent Interactions versus Steric Confinement in Asymmetric Supramolecular Catalysis.Journal of the American Chemical Society · 2026Article
- Size and Polarizability as Design Principles for Stereoselective Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- London Dispersion as a Design Element in Molecular Catalysis.Journal of the American Chemical Society · 2025Review
- A Quantum Chemical Method for Dissecting London Dispersion Energy into Atomic Building Blocks.ACS central science · 2025Article
- From Reagent to Catalyst: Dispersion-Driven Design of a General Asymmetric Transfer Hydrogenation Catalyst.Journal of the American Chemical Society · 2025Article
- London dispersion forces and steric effects within nanocomposites tune interaction energies and chain conformation.Communications chemistry · 2025Article
- Highly Acidic Electron-Rich Brønsted Acids Accelerate Asymmetric Pictet-Spengler Reactions by Virtue of Stabilizing Cation-π Interactions.Journal of the American Chemical Society · 2024Article
- Efficient synthesis of (±)-de-Tetrahedron letters · 2024Article
- The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
- Local Energy Decomposition Analysis of London Dispersion Effects: From Simple Model Dimers to Complex Biomolecular Assemblies.Accounts of chemical research · 2024Article
- Polarizability matters in enantio-selection.Nature communications · 2024Article
- Dimerization of confined Brønsted acids in enantioselective organocatalytic reactions.Chemical science · 2023Article
- Catalytic Asymmetric Hydrogen Atom Transfer: Enantioselective Hydroamination of Alkenes.Journal of the American Chemical Society · 2023Article
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3 authors.
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Abstract
The well-known Corey-Bakshi-Shibata (CBS) reduction is a powerful method for the asymmetric synthesis of alcohols from prochiral ketones, often featuring high yields and excellent selectivities. While steric repulsion has been regarded as the key director of the observed high enantioselectivity for many years, we show that London dispersion (LD) interactions are at least as important for enantiodiscrimination. We exemplify this through a combination of detailed computational and experimental studies for a series of modified CBS catalysts equipped with dispersion energy donors (DEDs) in the catalysts and the substrates. Our results demonstrate that attractive LD interactions between the catalyst and the substrate, rather than steric repulsion, determine the selectivity. As a key outcome of our study, we were able to improve the catalyst design for some challenging CBS reductions.
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