2014 年 72 巻 8 号 p. 919-928
A novel and efficient method for the kinetic resolution of racemic alcohols with achiral carboxylic acids or racemic carboxylic acids with achiral alcohols using dehydration condensation is accounted in this paper. The first kinetic resolution of racemic alcohols with achiral carboxylic acids was accomplished by asymmetric esterification via the in situ formation of a mixed anhydride using carboxylic anhydrides as coupling reagents in the presence of chiral acyl-transfer catalysts. Because this protocol utilized the transacylation process to generate the mixed-anhydride, not only racemic secondary alcohols but also racemic carboxylic acids are applicable to the asymmetric esterification in the same manner. The variety of optically active carboxylic esters are also produced by the kinetic resolution of racemic 2-arylalkanoic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), with achiral alcohols, using carboxylic anhydrides in the presence of chiral acyl-transfer catalysts.