Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches

Annemarie Hage, Daniëlle G.I. Petra, Jim A. Field, Dick Schipper, Joannes B.P.A. Wijnberg, Paul C.J. Kamer, Joost N.H. Reek, Piet W.N.M. Van Leeuwen, Ron Wever, Hans E. Schoemaker

Research output: Contribution to journalArticlepeer-review

69 Scopus citations

Abstract

Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)-amino alcohol and iridium(I)-amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98%). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol.

Original languageEnglish (US)
Pages (from-to)1025-1034
Number of pages10
JournalTetrahedron Asymmetry
Volume12
Issue number7
DOIs
StatePublished - May 8 2001

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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