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

Xingwei Guo, Yasunori Okamoto, Mirjam R. Schreier, Thomas R. Ward, Oliver S. Wenger

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5052-5056
Number of pages5
JournalChemical Science
Volume9
Issue number22
DOIs
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network'. Together they form a unique fingerprint.

Cite this