ArticleAngewandte Chemie (International ed. in English)2018
Highly Diastereo- and Enantioselective Synthesis of Nitrile-Substituted Cyclopropanes by Myoglobin-Mediated Carbene Transfer Catalysis.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
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Who cites it
39 citing papers in PubMed, 104 citations in OpenAlex.
- Alkynyltriazenes in Photochemical Metal-Free Doyle-Kirmse Rearrangements.Angewandte Chemie (International ed. in English) · 2026Article
- Computational design of generalist cyclopropanases with stereodivergent selectivity.Nature communications · 2026Article
- Highly Enantioselective Synthesis of Halogenated Cyclopropanes via Enzyme Catalyzed Carbene Transfer.ChemCatChem · 2025Article
- Nitrogen Insertion via Asymmetric Condensation and Chirality Transfer: A Stereodivergent Entry to Cyanocyclopropanes.Angewandte Chemie (International ed. in English) · 2025Article
- Automated Flow Synthesis of Artificial Heme Enzymes for Enantiodivergent Biocatalysis.Journal of the American Chemical Society · 2025Article
- Production of Phenyldiazene Derivatives Using the Biosynthetic Pathway of an Aromatic Diazo Group-Containing Natural Product from an Actinomycete.Chembiochem : a European journal of chemical biology · 2025Article
- Hybrid Metal Catalysts as Valuable Tools in Organic Synthesis: An Overview of the Recent Advances in Asymmetric C─C Bond Formation Reactions.Molecules (Basel, Switzerland) · 2024Review
- Biocatalytic Strategy for the Highly Stereoselective Synthesis of Fluorinated Cyclopropanes.Angewandte Chemie (International ed. in English) · 2024Article
- Stereodivergent Synthesis of Pyridyl Cyclopropanes via Enzymatic Activation of Pyridotriazoles.Journal of the American Chemical Society · 2024Article
- Biocatalytic strategy for the construction of spNature chemistry · 2024Article
- Chemoenzymatic synthesis of optically active α-cyclopropyl-pyruvates and cyclobutenoates via enzyme-catalyzed carbene transfer with diazopyruvate.Organic chemistry frontiers : an international journal of organic chemistry · 2024Article
- Biocatalytic, Stereoconvergent Alkylation of (Nature synthesis · 2024Article
- 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
- Enantio- and Diastereoenriched Enzymatic Synthesis of 1,2,3-Polysubstituted Cyclopropanes from (Z/E)-Trisubstituted Enol Acetates.Research square · 2023Article
- Chemodivergent C(spNature catalysis · 2023Article
- Article
- Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.Chemical science · 2022Review
- Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions.Bulletin of Japan Society of Coordination Chemistry · 2022Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
A chemobiocatalytic strategy for the highly stereoselective synthesis of nitrile-substituted cyclopropanes is reported. The present approach relies on an asymmetric olefin cyclopropanation reaction catalyzed by an engineered myoglobin in the presence of ex situ generated diazoacetonitrile within a compartmentalized reaction system. This method enabled the efficient transformation of a broad range of olefin substrates at a preparative scale with up to 99.9 % de and ee and up to 5600 turnovers. The enzymatic product could be further elaborated to afford a variety of functionalized chiral cyclopropanes. This work expands the range of synthetically valuable, abiotic transformations accessible through biocatalysis and paves the way to the practical and safe exploitation of diazoacetonitrile in biocatalytic carbene transfer reactions.
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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.