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Enantioselective Synthesis of Amines by Combining Photoredox and Enzymatic Catalysis in a Cyclic Reaction Network

Guo, Xingwei and Okamoto, Yasunori and Schreier, Mirjam R. and Ward, Thomas R. and Wenger, Oliver S.. (2018) Enantioselective Synthesis of Amines by Combining Photoredox and Enzymatic Catalysis in a Cyclic Reaction Network. Chemical Science, 9. pp. 5052-5056.

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Anorganische Chemie (Wenger)
05 Faculty of Science > Departement Chemie > Chemie > Bioanorganische Chemie (Ward)
UniBasel Contributors:Wenger, Oliver and Guo, Xingwei and Okamoto, Yasunori and Schreier, Mirjam and Ward, Thomas R. R.
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:2041-6520
e-ISSN:2041-6539
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:11 Jun 2018 13:21
Deposited On:11 Jun 2018 13:21

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