Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation–Racemization and Enzymatic Resolution Cascade

Osama El-Sepelgy*, Aleksandra Brzozowska, Magnus Rueping

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation–dehydrogenation–hydrogenation of prochiral ketones. By merging the iron-catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones, as well as diketones, were reductively acylated. The corresponding products were isolated with high yields and enantioselectivities. The use of an iron catalyst together with molecular hydrogen as the hydrogen donor and readily available ethyl acetate as acyl donor make this cascade process highly interesting in terms of both economic value and environmental credentials.

Original languageEnglish (US)
Pages (from-to)1664-1668
Number of pages5
JournalCHEMSUSCHEM
Volume10
Issue number8
DOIs
StatePublished - Apr 22 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • cascade catalysis
  • chiral alcohols
  • enzyme
  • kinetic resolution
  • racemization

ASJC Scopus subject areas

  • General Chemical Engineering
  • General Energy
  • General Materials Science
  • Environmental Chemistry

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