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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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Supplementary files

Article information


Submitted
05 Apr 2018
Accepted
05 May 2018
First published
17 May 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5052-5056
Article type
Edge Article

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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