Baker’s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARα ligands

Add time:07/12/2019    Source:sciencedirect.com

Several 2-(4-chlorophenoxy)-3-oxoesters were prepared in fair to good yields and then reduced in the presence of baker’s yeast to the corresponding alcohols having de’s up to 92% and ee’s >99%. The absolute configuration of nearly enantiomerically pure ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate was assigned by both comparison of the sign of the specific rotation and HPLC retention times of authentic samples prepared from threonines. Reduction of ethyl 2-(4-chlorophenoxy)-3-oxo-4-phenylbutanoate afforded only enantiomerically pure ethyl (2R,3S)-2-(4-chlorophenoxy)-3-hydroxy-4-phenylbutanoate (out of the four possible stereoisomers), whose absolute configuration was established by single crystal X-ray analysis. Furthermore, reduction of ethyl 2-methyl-2-(4-chlorophenoxy)-3-hydroxybutanoate with a quaternary stereogenic carbon (C2) gave both of the two expected diastereoisomers with ee = 95% and 96%. Insight into the mechanism of baker’s yeast-mediated reduction of prochiral ketoesters is also reported.

We also recommend Trading Suppliers and Manufacturers of ethyl 4-(4-chlorophenoxy)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (cas 439097-52-6). Pls Click Website Link as below: cas 439097-52-6 suppliers

Prev:Functionalized erythro N-protected α-amino epoxides. Stereocontrolled synthesis and biological activity
Next:Diastereo- and enantioselective bioreduction of ethyl 2-(4-chlorophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts)