ArticleOrganic letters2018
Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.
Article in Organic letters, 2018. 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.
- A facile preparation method for homogeneous Ir catalysts for dehydrogenation and hydrogenation reactions involving N-heteroarenes.RSC advances · 2025Article
- Synthesis and crystal structure of piperidinyl propanenitrile towards the preparation of piperidine based bioactive films for drug delivery applications.Scientific reports · 2025Article
- Reductive Transamination of Pyridinium Salts to N-Aryl Piperidines.The Journal of organic chemistry · 2024Article
- A Novel Natural Siderophore Antibiotic Conjugate Reveals a Chemical Approach to Macromolecule Coupling.ACS central science · 2023Article
- Asymmetric arene hydrogenation: towards sustainability and application.Chemical Society reviews · 2023Review
- Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications.International journal of molecular sciences · 2023Review
- Synthesis of Stereoenriched Piperidines via Chemo-Enzymatic Dearomatization of Activated Pyridines.Journal of the American Chemical Society · 2022Article
- Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources.Nature communications · 2022Article
- Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation.Chemical reviews · 2022Review
- Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.Chemical science · 2021Article
- Recent Advances in Homogeneous Catalysts for the Asymmetric Hydrogenation of Heteroarenes.ACS catalysis · 2020Article
- Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.Angewandte Chemie (International ed. in English) · 2019Review
- Secondary amines as coupling partners in direct catalytic asymmetric reductive amination.Chemical science · 2019Article
- A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes.Chemical science · 2019Article
- Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ACS catalysis · 2018Article
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21 authors.
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Abstract
Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of α-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.
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