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Issue 22, 2018
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Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network

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Abstract

Visible light-driven reduction of imines to enantioenriched amines in aqueous solution is demonstrated for the first time. Excitation of a new water-soluble variant of the widely used [Ir(ppy)3] (ppy = 2-phenylpyridine) photosensitizer in the presence of a cyclic imine affords a highly reactive α-amino alkyl radical that is intercepted by hydrogen atom transfer (HAT) from ascorbate or thiol donors to afford the corresponding amine. The enzyme monoamine oxidase (MAO-N-9) selectively catalyzes the oxidation of one of the enantiomers to the corresponding imine. Upon combining the photoredox and biocatalytic processes under continuous photo-irradiation, enantioenriched amines are obtained in excellent yields. To the best of our knowledge, this is the first demonstration of a concurrent photoredox- and enzymatic catalysis leading to a light-driven asymmetric synthesis of amines.

Graphical abstract: Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network

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Publication details

The article was received on 05 Apr 2018, accepted on 05 May 2018 and first published on 17 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01561A
Citation: Chem. Sci., 2018,9, 5052-5056
  • Open access: Creative Commons BY-NC license
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    Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network

    X. Guo, Y. Okamoto, M. R. Schreier, T. R. Ward and O. S. Wenger, Chem. Sci., 2018, 9, 5052
    DOI: 10.1039/C8SC01561A

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