ArticleNature communications2020
Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 115 citations in OpenAlex.
- Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis.Molecules (Basel, Switzerland) · 2025Article
- Dual NHC/HAT-Promoted Esterification to Access α-Aryl Glycines.Advanced synthesis & catalysis · 2025Article
- Nickel-catalyzed asymmetric hydrogenation for the preparation of α-substituted propionic acids.Nature communications · 2024Article
- C(sp)-C(sp) Lever-Based Targets of Orientational Chirality: Design and Asymmetric Synthesis.Molecules (Basel, Switzerland) · 2024Article
- Amino Turbo Chirality and Its Asymmetric Control.Research (Washington, D.C.) · 2024Article
- Discovery of Staircase Chirality through the Design of Unnatural Amino Acid Derivatives.Research (Washington, D.C.) · 2024Article
- Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction.Molecules (Basel, Switzerland) · 2023Review
- Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis.Organic letters · 2023Article
- Formal [3 + 2] Cycloaddition ofMolecules (Basel, Switzerland) · 2023Article
- Asymmetric Hydrogenation of Tetrasubstituted α,β-Unsaturated Ketones: Access to Chiral 2‑Substituted Cyclopentyl Aryl Ketones.Precision chemistry · 2023Article
- Co-Catalyzed Asymmetric Hydrogenation. The Same Enantioselection Pattern for Different Mechanisms.International journal of molecular sciences · 2023Article
- Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates.Research (Washington, D.C.) · 2023Article
- The Origin of Stereoselectivity in the Hydrogenation of Oximes Catalyzed by Iridium Complexes: A DFT Mechanistic Study.Molecules (Basel, Switzerland) · 2022Article
- Nickel-catalysed asymmetric hydrogenation of oximes.Nature chemistry · 2022Article
- Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketals.Nature communications · 2022Article
- Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation.Chemical reviews · 2022Review
- Orientational Chirality, Its Asymmetric Control, and Computational Study.Research (Washington, D.C.) · 2022Article
- A new chiral phenomenon of orientational chirality, its synthetic control and computational study.Frontiers in chemistry · 2022Article
- Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.Chemical science · 2021Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral α-aryl glycines play a key role in the preparation of some bioactive products, however, their catalytic asymmetric synthesis is far from being satisfactory. Herein, we report an efficient nickel-catalyzed asymmetric hydrogenation of N-aryl imino esters, affording chiral α-aryl glycines in high yields and enantioselectivities (up to 98% ee). The hydrogenation can be conducted on a gram scale with a substrate/catalyst ratio of up to 2000. The obtained chiral N-p-methoxyphenyl α-aryl glycine derivatives are not only directly useful chiral secondary amino acid esters but can also be easily deprotected by treatment with cerium ammonium nitrate for further transformations to several widely used molecules including drug intermediates and chiral ligands. Formation of a chiral Ni-H species in hydrogenation is detected by
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