ArticleNature chemistry2022
Nickel-catalysed asymmetric hydrogenation of oximes.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Monosubstituted N-Arylhydroxylamine Chemistry: Integrating Contemporary Synthetic Approaches for the Efficient Construction of Diverse Heterocyclic Scaffolds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
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- Electrocatalytic Nitrate Reduction to Hydroxylamine: Breaking the Activity-Selectivity Trade-Off by Designer Bifunctional Metal-Organic Frameworks.Angewandte Chemie (International ed. in English) · 2026Article
- Iridium-Catalyzed Regio- and Enantioselective Hydrogenation of 5‑Alkylidene Cyclopentenones.Precision chemistry · 2026Article
- Computational Analysis of the Asymmetric Hydrogenation of γ-Ketoacids: Weak Interactions and Kinetics.Molecules (Basel, Switzerland) · 2026Article
- Noncovalent interaction-driven regio- and enantioselective hydroalkynylation of unactivated alkenes to access remote chiral nitriles.Science advances · 2025Article
- Enantioselective NHC-Catalyzed Annulation via Umpolung for the Construction of Hydroxylamine Architectures with Variable Ring Sizes.Organic letters · 2025Article
- La(OCOCFACS omega · 2025Article
- Hydroxyl and nitrate co-upgrading to oxime via anode-cathode cascade electrolyzer.Nature communications · 2025Article
- Ceria-Zirconia-Supported Pt as an Efficient Catalyst for the Sustainable Synthesis of Hydroxylamines and Primary Amines via the Hydrogenation of Oximes Under Ambient Conditions.Molecules (Basel, Switzerland) · 2025Article
- Modular synthesis of bis-α-chiral amines using Ellman sulfinamide for consecutiveScience advances · 2025Article
- Catalytic Reduction of Aromatic Nitro Compounds to Phenylhydroxylamine and Its Derivatives.Molecules (Basel, Switzerland) · 2024Review
- Article
- Nickel-catalyzed asymmetric hydrogenation for the preparation of α-substituted propionic acids.Nature communications · 2024Article
- Catalytic Asymmetric Access to Structurally DiverseJACS Au · 2024Article
- Catalytic Enantioselective Alkyne Addition to Nitrones Enabled by Tunable Axially Chiral Imidazole-Based P,N-Ligands.Journal of the American Chemical Society · 2024Article
- Article
- High-Grade Ferronickel Concentrates Prepared from Laterite Nickel Ore by a Carbothermal Reduction and Magnetic Separation Method.Materials (Basel, Switzerland) · 2023Article
- Article
- A 13-million turnover-number anionic Ir-catalyst for a selective industrial route to chiral nicotine.Nature communications · 2023Article
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral hydroxylamines are vital substances in bioscience and versatile subunits in the preparation of a variety of functional molecules. However, asymmetric and non-asymmetric synthetic approaches to these compounds are far from satisfactory. Although atom-economic metal-catalysed asymmetric hydrogenations have been studied for over 50 years, the asymmetric hydrogenation of oximes to the corresponding chiral hydroxylamines remains challenging because of the labile N-O bond and inert C=N bond. Here we report an environmentally friendly, earth-abundant, transition-metal nickel-catalysed asymmetric hydrogenation of oximes, affording the corresponding chiral hydroxylamines with up to 99% yield, 99% e.e. and with a substrate/catalyst ratio of 1,000. Computational results indicate that the weak interactions between the catalyst and substrate play crucial roles not only in the transition states, but also during the approach of the substrate to the catalyst, by selectively reducing the reaction barriers and thus improving the reaction efficiency and securing the generation of chirality.
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