Waagen V, Partali V, Hollingsaeter I, Huang M S, Anthonsen T
Department of Chemistry, University of Trondheim, Norway.
Acta Chem Scand (Cph). 1994 Jun;48(6):506-10. doi: 10.3891/acta.chem.scand.48-0506.
The stereoselectivity of Baker's yeast reduction of prochiral alpha-oxygenated 2-propanones has been studied by varying the substrate structure. The 1-hydroxy-3-methoxy-3-propanone 1a was reduced to the corresponding alcohol (R)-2a with 88% enantiomeric excess. Replacing the hydroxy group in 1a with phenoxy or benzyloxy (1b and 1c) gave the alcohols (S)-2b and (S)-2c with 53 and 32% ee, respectively. Reduction of the methyl ketone 1d gave the alcohol (S)-2d with 91% ee. Attempts to improve the enantioselectivity of the reduction of 1c by lowering the substrate concentration or addition of selective reductase inhibitors had only small effect on the enantioselectivity.
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