Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis

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

Research output: Contribution to journalReview articlepeer-review

10 Citations (Scopus)

Abstract

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 α-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.

Original languageEnglish
Pages (from-to)1288-1293
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number10
DOIs
Publication statusPublished - 2020 Mar 15

Keywords

  • Asymmetric synthesis
  • Electron transfer
  • Enzyme catalysis
  • Photocatalysis
  • Photochemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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