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

• Published in: Tetrahedron: asymmetry Vol. 12; no. 7; pp. 1025 - 1034
• Main Authors: Hage, Annemarie, Petra, Daniëlle G.I, Field, Jim A, Schipper, Dick, Wijnberg, Joannes B.P.A, Kamer, Paul C.J, Reek, Joost N.H, van Leeuwen, Piet W.N.M, Wever, Ron, Schoemaker, Hans E
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 08-05-2001
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(01)00172-0

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.
Biotransformations using whole cells of
Merulius tremellosus, asymmetric transfer hydrogenation using homochiral Ru and Ir catalysts.