ArticleJournal of the American Chemical Society2018
Cyclopropanations via Heme Carbenes: Basic Mechanism and Effects of Carbene Substituent, Protein Axial Ligand, and Porphyrin Substitution.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 55 papers.
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Who cites it
55 citing papers in PubMed, 155 citations in OpenAlex.
- Direct Access to Iron Carbenes from Aldehyde, Ketone, and Formamide Feedstocks.Journal of the American Chemical Society · 2026Article
- Photoredox-Neutral Platform for Direct Decarboxylative CyclopropanationACS catalysis · 2026Article
- Catalyst-Free Electro-photochemical Hydroalkylation ofJACS Au · 2026Article
- Computational design of generalist cyclopropanases with stereodivergent selectivity.Nature communications · 2026Article
- Chemoenzymatic Diazo Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases.Journal of the American Chemical Society · 2026Article
- Hydrogen-deuterium exchange reveals catalytically linked protein flexibility in myoglobin-mediated intramolecular C(spProtein science : a publication of the Protein Society · 2026Article
- Oxidative HNO Formation Mechanisms from NHACS omega · 2025Article
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- Mechanistic investigation of sustainable heme-inspired biocatalytic synthesis of cyclopropanes for challenging substrates.Communications chemistry · 2024Article
- Radical-Mediated Regiodivergent C(Chem catalysis · 2024Article
- One-Electron NO to NChemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Noncanonical Amino Acids: Bringing New-to-Nature Functionalities to Biocatalysis.Chemical reviews · 2024Review
- Stereodivergent Synthesis of Pyridyl Cyclopropanes via Enzymatic Activation of Pyridotriazoles.Journal of the American Chemical Society · 2024Article
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- Biocatalytic strategy for the construction of spNature chemistry · 2024Article
- Mechanistic manifold in a hemoprotein-catalyzed cyclopropanation reaction with diazoketone.Nature communications · 2023Article
- Iron(III)-based metalloradical catalysis for asymmetric cyclopropanation via a stepwise radical mechanism.Nature chemistry · 2023Article
- Role of mutations in a chemoenzymatic enantiodivergent C(spChemical science · 2023Article
- Enantio- and Diastereoenriched Enzymatic Synthesis of 1,2,3-Polysubstituted Cyclopropanes from (Journal of the American Chemical Society · 2023Article
- Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters.The Journal of organic chemistry · 2023Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Catalytic carbene transfer to olefins is a useful approach to synthesize cyclopropanes, which are key structural motifs in many drugs and biologically active natural products. While catalytic methods for olefin cyclopropanation have largely relied on rare transition-metal-based catalysts, recent studies have demonstrated the promise and synthetic value of iron-based heme-containing proteins for promoting these reactions with excellent catalytic activity and selectivity. Despite this progress, the mechanism of iron-porphyrin and hemoprotein-catalyzed olefin cyclopropanation has remained largely unknown. Using a combination of quantum chemical calculations and experimental mechanistic analyses, the present study shows for the first time that the increasingly useful C═C functionalizations mediated by heme carbenes feature an Fe
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