ArticleNature chemistry2019
Unravelling mechanistic features of organocatalysis with in situ modifications at the secondary sphere.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Towards next generation enzyme mimics through local electric field control in organic cage catalysts.Chemical science · 2026Article
- Cooperative NHC and Photoredox Dual Catalysis for the Construction of Carbonyl Compounds.ACS omega · 2026Review
- AI Approaches to Homogeneous Catalysis with Transition Metal Complexes.ACS catalysis · 2025Review
- Machine learning workflows beyond linear models in low-data regimes.Chemical science · 2025Article
- Recent advances in the use of N-heterocyclic carbene adducts of N, P, C elements as supporting ligands in organometallic chemistry.RSC advances · 2025Review
- Intelligent design and synthesis of energy catalytic materials.Fundamental research · 2025Review
- Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds.Beilstein journal of organic chemistry · 2025Review
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- Electrostatic Interactions in Asymmetric Organocatalysis.Accounts of chemical research · 2023Article
- ElectrostaticChemical science · 2022Article
- Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Effect of Solvents on Proline Modified at the Secondary Sphere: A Multivariate Exploration.The Journal of organic chemistry · 2022Article
- Electric Fields in Catalysis: From Enzymes to Molecular Catalysts.ACS catalysis · 2021Article
- Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts.Chemical science · 2021Article
- Association Equilibria of Organo-Phosphoric Acids with Imines from a Combined Dielectric and Nuclear Magnetic Resonance Spectroscopy Approach.Analytical chemistry · 2021Article
- Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.Chemical reviews · 2020Review
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Secondary-sphere interactions serve a fundamental role in controlling the reactivity and selectivity of organometallic and enzymatic catalysts. However, there is a dearth of studies that explicitly incorporate secondary-sphere modifiers into organocatalytic systems. In this work, we introduce an approach for the in situ systematic modification of organocatalysts in their secondary sphere through dynamic covalent binding under the reaction conditions. As a proof-of-concept, we applied boronic acids as secondary-sphere modifiers of N-heterocyclic carbenes that contained a hydroxy handle. The bound system formed in the reaction mixture catalysed the enantioselective benzoin condensations of a challenging substrate class that contains electron-withdrawing groups. Linear regression coupled with data visualization served to pinpoint the divergent origins of enantioselectivity for different substrates and decision tree algorithms served to formulate selection criteria for the appropriate secondary-sphere modifiers. The combination of this highly modular catalytic approach with machine-learning techniques provided mechanistic insights and guided the streamlined optimization process of a gram-scale reaction at low organocatalyst loading.
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Registered trials
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