ArticleJournal of the American Chemical Society2022
Synthesis of Stereoenriched Piperidines via Chemo-Enzymatic Dearomatization of Activated Pyridines.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
16 citing papers in PubMed, 45 citations in OpenAlex.
- Photocatalytic Annulation of Primary Amines to δ-Lactams: Access to Privileged (Spiro)piperidine Space.Organic letters · 2026Article
- Reprogramming Imine Reductases for Enantioselective Reduction of Electron-Rich Enamides.JACS Au · 2026Article
- Alcohol Oxidase-Imine Reductase Cascade for One-Pot Chiral Amine Synthesis.ACS catalysis · 2026Article
- An organometallic approach to the synthesis of heteropolycyclic compounds from benzenes.Nature communications · 2025Article
- Engineered Biocatalyst for Enantioselective Hydrazone Reduction.Angewandte Chemie (International ed. in English) · 2025Article
- Deconstruction of Desacetamidocolchicine's B Ring Reveals a Class 3 Atropisomeric AC Ring with Tubulin Binding Properties.The Journal of organic chemistry · 2025Article
- Bifunctional Imine Reductase Cascades for the Synthesis of SaturatedACS catalysis · 2024Article
- The Impact of Metagenomics on Biocatalysis.Angewandte Chemie (International ed. in English) · 2024Review
- Multifunctional Biocatalysts for Organic Synthesis.Journal of the American Chemical Society · 2024Review
- Rhodium-Catalyzed Asymmetric Functionalization of Quinoxalinium Salts.Organic letters · 2023Article
- Biocatalysis in Drug Design: Engineered Reductive Aminases (RedAms) Are Used to Access Chiral Building Blocks with Multiple Stereocenters.Journal of the American Chemical Society · 2023Article
- Palladium-Catalyzed Arylation of Endocyclic 1-Azaallyl Anions: Concise Synthesis of Unprotected Enantioenriched cis-2,3-Diarylpiperidines.Angewandte Chemie (International ed. in English) · 2023Article
- Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines.Molecules (Basel, Switzerland) · 2023Review
- Article
- Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine.Journal of the American Chemical Society · 2023Article
- Synthesis of Dihydropyridine Spirocycles by Semi-Pinacol-Driven Dearomatization of Pyridines.Organic letters · 2023Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
14 authors at 3 institutions in 1 country.
Funding
Abstract
The development of efficient and sustainable methods for the synthesis of nitrogen heterocycles is an important goal for the chemical industry. In particular, substituted chiral piperidines are prominent targets due to their prevalence in medicinally relevant compounds and their precursors. A potential biocatalytic approach to the synthesis of this privileged scaffold would be the asymmetric dearomatization of readily assembled activated pyridines. However, nature is yet to yield a suitable biocatalyst specifically for this reaction. Here, by combining chemical synthesis and biocatalysis, we present a general chemo-enzymatic approach for the asymmetric dearomatization of activated pyridines for the preparation of substituted piperidines with precise stereochemistry. The key step involves a stereoselective one-pot amine oxidase/ene imine reductase cascade to convert N-substituted tetrahydropyridines to stereo-defined 3- and 3,4-substituted piperidines. This chemo-enzymatic approach has proved useful for key transformations in the syntheses of antipsychotic drugs Preclamol and OSU-6162, as well as for the preparation of two important intermediates in synthetic routes of the ovarian cancer monotherapeutic Niraparib.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.