Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis

Guo, Xingwei and Okamoto, Yasunori and Schreier, Mirjam R. and Ward, Thomas R. and Wenger, Oliver S.. (2019) Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis. European Journal of Organic Chemistry.

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Official URL: https://edoc.unibas.ch/72319/

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Photochemistry usually functions on a one-photon-one-electron basis, leading to unstable radical intermediates that must be intercepted rapidly to allow efficient product formation. This can render multi-electron reductions and enantioselective reactions particularly challenging. In this minireview, we discuss recent advances in the area of photo-driven multi-electron transfer with a particular focus on our own work on reductive amination and the enantioselective synthesis of amines by combined photoredox and enzyme catalysis. Polarity-matched hydrogen atom transfer (HAT) between photochemically-generated alpha-amino alkyl radicals and thiols is a key step in these reactions. A cyclic reaction network comprised of light-driven imine reduction by an Ir-photocatalyst and enantioselective amine oxidation by the enzyme monoamine oxidase (MAO-N-9) was used to obtain enantioenriched amines from imines.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Bioanorganische Chemie (Ward)
UniBasel Contributors:Guo, Xingwei and Okamoto, Yasunori and Schreier, Mirjam and Ward, Thomas R. R. and Wenger, Oliver
Item Type:Article, refereed
Article Subtype:Further Journal Contribution
Note:Publication type according to Uni Basel Research Database: Journal item
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Last Modified:20 Jan 2021 09:54
Deposited On:29 Oct 2019 14:42

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