Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Juraj Paris, Aline Telzerow, Nicolás Ríos-Lombardía, Kerstin Steiner, Helmut Schwab, Francisco Morís, Harald Gröger*, Javier González-Sabín

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

Original languageEnglish
Pages (from-to)5486-5493
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number5
DOIs
Publication statusPublished - 4 Mar 2019

Keywords

  • Amines
  • Asymmetric synthesis
  • Biocatalysis
  • Deep eutectic solvents
  • Palladium catalysis
  • Suzuki cross-coupling reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

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