ArticleACS catalysis2020
Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion.
Article in ACS catalysis, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 53 citations in OpenAlex.
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- Mechanistic manifold in a hemoprotein-catalyzed cyclopropanation reaction with diazoketone.Nature communications · 2023Article
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- Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.Chemical science · 2022Review
- Tandem Friedel-Crafts-Alkylation-Enantioselective-Protonation by Artificial Enzyme Iminium Catalysis.ChemCatChem · 2022Article
- Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.Journal of the American Chemical Society · 2022Article
- Enantioselective Synthesis of α-Trifluoromethyl Amines via Biocatalytic N-H Bond Insertion with Acceptor-Acceptor Carbene Donors.Journal of the American Chemical Society · 2022Article
- Directed Evolution of Artificial Metalloenzymes in Whole Cells.Angewandte Chemie (International ed. in English) · 2022Article
- Dual-function enzyme catalysis for enantioselective carbon-nitrogen bond formation.Nature chemistry · 2021Article
- Controllable stereoinversion in DNA-catalyzed olefin cyclopropanationChemical science · 2021Article
- Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Optically active amines represent highly valuable building blocks for the synthesis of advanced pharmaceutical intermediates, drug molecules, and biologically active natural products. Hemoproteins have recently emerged as promising biocatalysts for the formation of C-N bonds via carbene transfer, but asymmetric N-H carbene insertion reactions using these or other enzymes have so far been elusive. Here, we report the successful development of a biocatalytic strategy for the asymmetric N-H carbene insertion of aromatic amines with 2-diazopropanoate esters using engineered variants of myoglobin. High activity and stereoinduction in this reaction could be achieved by tuning the chiral environment around the heme cofactor in the metalloprotein in combination with catalyst-matching and tailoring of the diazo reagent. Using this approach, an efficient biocatalytic protocol for the synthesis of a broad range of substituted aryl amines with up to 82%
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