Aerobic C−N Bond Formation through Enzymatic Nitroso-Ene-Type Reactions
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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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Date
2023-02-06
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Language
en
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Angewandte Chemie - International Edition, articlenumber e202213671
Abstract
The biocatalytic oxidation of acylated hydroxylamines enables the direct and selective introduction of nitrogen functionalities by activation of allylic C−H bonds. Utilizing either laccases or an oxidase/peroxidase couple for the formal dehydrogenation of N-hydroxycarbamates and hydroxamic acids with air as the terminal oxidant, acylnitroso species are generated under particularly mild aqueous conditions. The reactive intermediates undergo C−N bond formation through an ene-type mechanism and provide high yields both in intramolecular and intermolecular enzymatic aminations. Investigations on different pathways of the two biocatalytic systems and labelling studies provide more insight into this unprecedented promiscuity of classical oxidoreductases as catalysts for nitroso-based transformations.Description
| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (298250 & 324976), and the Ruth & Nils‐Erik Stenbäcks Stiftelse. C.J. thanks the Aalto School of Chemical Technology, as well as the Finnish Foundation for Technology Promotion and the Orion Research Foundation for personal grants. Publisher Copyright: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Keywords
Amination, Biocatalysis, Cyclization, Ene Reaction, Heterocycles
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Citation
Jäger, C, Haase, M, Koschorreck, K, Urlacher, V B & Deska, J 2023, ' Aerobic C−N Bond Formation through Enzymatic Nitroso-Ene-Type Reactions ', Angewandte Chemie - International Edition, vol. 62, no. 7, e202213671 . https://doi.org/10.1002/anie.202213671
