Stereoselectivity of Baker's yeast reduction of 2-propanones: influence of substituents.
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.
Waagen
V
V
Department of Chemistry, University of Trondheim, Norway.
Partali
V
V
Hollingsaeter
I
I
Huang
M S
MS
Anthonsen
T
T
D000096:Acetone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D000096:Acetone