Stereospecific hydrolysis of 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase

In the hydrolysis of racemic 3-(4-methoxyphenyi)glycidic acid methyl ester by immobilized Mucor miehei lipase in supercritical CO2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S)-form. The stereoisomeric excess of the (2R,3S)-form reached 87% at 53% total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO2 was considerably faster than in toluene/water-mixture.