821783-51-1Relevant articles and documents
Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: Synthesis of clofibrate analogues
Perrone, Maria Grazia,Santandrea, Ernesto,Di Nunno, Leonardo,Scilimati, Antonio,Tortorella, Vincenzo,Capitelli, Francesco,Bertolasi, Valerio
, p. 783 - 792 (2007/10/03)
Clofibrate is a well-known peroxisome proliferator-activated receptor-α (PPARα) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of e
Baker's yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3- oxoalkanoates intermediates for potential PPARα ligands
Perrone, Maria Grazia,Santandrea, Ernesto,Scilimati, Antonio,Tortorella, Vincenzo,Capitelli, Francesco,Bertolasi, Valerio
, p. 3501 - 3510 (2007/10/03)
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.
