TY - JOUR
T1 - Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation
T2 - Complementary approaches
AU - Hage, Annemarie
AU - Petra, Daniëlle G.I.
AU - Field, Jim A.
AU - Schipper, Dick
AU - Wijnberg, Joannes B.P.A.
AU - Kamer, Paul C.J.
AU - Reek, Joost N.H.
AU - Van Leeuwen, Piet W.N.M.
AU - Wever, Ron
AU - Schoemaker, Hans E.
N1 - Funding Information:
This investigation was supported by the Innovation Oriented Research Program on Catalysis of the Dutch Ministry of Economic Affairs.
PY - 2001/5/8
Y1 - 2001/5/8
N2 - 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.
AB - 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.
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U2 - 10.1016/S0957-4166(01)00172-0
DO - 10.1016/S0957-4166(01)00172-0
M3 - Article
AN - SCOPUS:0035826605
SN - 0957-4166
VL - 12
SP - 1025
EP - 1034
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 7
ER -