ArticleCommunications chemistry2019
Chemoenzymatic conversion of amides to enantioenriched alcohols in aqueous medium.
Article in Communications chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 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
15 citing papers in PubMed, 55 citations in OpenAlex.
- Chemoenzymatic synthesis.Communications chemistry · 2025Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Nickel-Catalyzed Suzuki-Miyaura Coupling in Water for the Synthesis of 2-Aryl Allyl Phosphonates and Sulfones.The Journal of organic chemistry · 2024Article
- Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide electrophiles.Chemical science · 2024Article
- Asymmetric α-benzylation of cyclic ketones enabled by concurrent chemical aldol condensation and biocatalytic reduction.Nature communications · 2024Article
- Opportunities and Challenges of Metal-Organic Framework Micro/Nano Reactors for Cascade Reactions.JACS Au · 2023Review
- Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.SynOpen (2017) · 2023Article
- Significant Enhancement of 5-Hydroxymethylfural Productivity fromMolecules (Basel, Switzerland) · 2022Article
- Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.Angewandte Chemie (International ed. in English) · 2021Article
- Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.ACS catalysis · 2020Article
- Treating a Global Health Crisis with a Dose of Synthetic Chemistry.ACS central science · 2020Article
- A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Nickel-Catalyzed Conversion of Amides to Carboxylic Acids.Organic letters · 2020Article
- Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.Organic letters · 2020Article
- Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
One-pot reactions that combine non-enzymatic and biocatalytic transformations represent an emerging strategy in chemical synthesis. Some of the most powerful chemoenzymatic methodologies, although uncommon, are those that form a carbon-carbon (C-C) bond and a stereocenter at one of the reacting carbons, thereby streamlining traditional retrosynthetic disconnections. Here we report the one-pot, chemoenzymatic conversion of amides to enantioenriched alcohols. This transformation combines a nickel-catalyzed Suzuki-Miyaura coupling of amides in aqueous medium with an asymmetric, biocatalytic reduction to provide diarylmethanol derivatives in high yields and enantiomeric excesses. The synthetic utility of this platform is underscored by the formal syntheses of both antipodes of the pharmaceutical orphenadrine, which rely on ketoreductase enzymes that instill complementary stereoselectivities. We provide an explanation for the origins of stereoselectivity based on an analysis of the enzyme binding pockets.
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.