ArticleAngewandte Chemie (International ed. in English)2021
Biocatalytic, Intermolecular C-H Bond Functionalization for the Synthesis of Enantioenriched Amides.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
What it found
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Who cites it
22 citing papers in PubMed, 65 citations in OpenAlex.
- Stereoselective Synthesis of Aminals Through Enzyme-Catalyzed Intermolecular C(spAngewandte Chemie (International ed. in English) · 2026Article
- Reaction Pathway and Axial Ligand Effects of C(spJACS Au · 2026Article
- Highly stereoselective synthesis of allylic β-lactamsChemical science · 2026Article
- Nonheme Fe 1,3-nitrogen migratases for asymmetric noncanonical amino acid synthesis.Nature chemical biology · 2025Article
- A biocompatible Lossen rearrangement in Escherichia coli.Nature chemistry · 2025Article
- Contextual Analysis of Scientific Publications for Advancing Writing Skills (CASPArS): Self-Learning for Science Writing Using Top Scientists' Literature.Journal of chemical education · 2025Article
- Radical-Mediated Regiodivergent C(Chem catalysis · 2024Article
- Enantioselective Nitrene Transfer to Hydrocinnamyl Alcohols and Allylic Alcohols Enabled by Systematic Exploration of the Structure of Ion-Paired Rhodium Catalysts.Journal of the American Chemical Society · 2024Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Stereoselective Construction of β-, γ-, and δ-Lactam Rings via Enzymatic C-H Amidation.Nature catalysis · 2024Article
- Biocatalytic Construction of Chiral Pyrrolidines and Indolines via Intramolecular C(spACS central science · 2023Article
- Recent developments for intermolecular enantioselective amination of non-acidic C(spChemical science · 2023Review
- Catalytic, asymmetric carbon-nitrogen bond formation using metal nitrenoids: from metal-ligand complexesChemical science · 2023Review
- Enzymatic Nitrogen Incorporation Using Hydroxylamine.Journal of the American Chemical Society · 2023Article
- Directed Evolution of an Iron(II)- and α-Ketoglutarate-Dependent Dioxygenase for Site-Selective Azidation of Unactivated Aliphatic C-H Bonds.Angewandte Chemie (International ed. in English) · 2023Article
- Using enzymes to tame nitrogen-centred radicals for enantioselective hydroamination.Nature chemistry · 2023Article
- Stereoselective Construction of β-, γ-, and δ-Lactam Rings via Enzymatic C-H Amidation.Research square · 2023Article
- Undirected biocatalytic amination of unactivated C(Chem catalysis · 2022Article
- Biocatalytic Intramolecular C-H aminations via Engineered Heme Proteins: Full Reaction Pathways and Axial Ligand Effects.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Enzymatic Nitrogen Insertion into Unactivated C-H Bonds.Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C-N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C-H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C-H functionalization.
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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.