ArticleAngewandte Chemie (International ed. in English)2019
Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Sustainable Biocatalytic Cascades: A Versatile Tool in the Synthesis of Natural Products With Therapeutic Potential.Chembiochem : a European journal of chemical biology · 2026Review
- Atroposelective Dearomative Cross-Coupling of Benzofuran Derivatives by Z-Selective Functionalization of the Vinyl C─O Bond.Angewandte Chemie (International ed. in English) · 2026Article
- Computational design of generalist cyclopropanases with stereodivergent selectivity.Nature communications · 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
- Stereodivergent Synthesis of Pyridyl Cyclopropanes via Enzymatic Activation of Pyridotriazoles.Journal of the American Chemical Society · 2024Article
- Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins.Molecules (Basel, Switzerland) · 2023Review
- Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters.The Journal of organic chemistry · 2023Article
- Biocatalytic Intramolecular C-H aminations via Engineered Heme Proteins: Full Reaction Pathways and Axial Ligand Effects.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Highly stereoselective and enantiodivergent synthesis of cyclopropylphosphonates with engineered carbene transferases.Chemical science · 2022Article
- Designing Artificial Metalloenzymes by Tuning of the Environment beyond the Primary Coordination Sphere.Chemical reviews · 2022Review
- Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans.Journal of the American Chemical Society · 2022Article
- Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions.Bulletin of Japan Society of Coordination Chemistry · 2022Article
- Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021Article
- Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes.Journal of the American Chemical Society · 2021Article
- New-to-nature chemistry from old protein machinery: carbene and nitrene transferases.Current opinion in biotechnology · 2021Review
- Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHFAngewandte Chemie (International ed. in English) · 2021Article
- Insight into the preferential N-bindingDalton transactions (Cambridge, England : 2003) · 2021Article
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4 authors.
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Abstract
2,3-Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo- and enantioselective construction of stereochemically rich 2,3-dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure-reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single-enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C-C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.
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