Easy Separation of Optically Active Products

Significance

The kinetic resolution by enzymatic hydrolysis of PEG-supported carbonates was reported. Thus, a water-soluble substrate 1 was prepared via immobilization of ()-1-phenylethanol onto a monomethoxy PEG₅₀₀₀ (MPEG₅₀₀₀; average Mw 5,000) through a phenylethyl carbonate linker. Enantioselective hydrolysis of 1 with PPL (porcine pancreas lipase) was performed in hexane/0.1 M phosphate buffer (pH 6.5) to give (R)-2 in 24% conversion with 99% ee (E value = 270). The hydrolysis of 5 under similar conditions afforded (R)-6 in 3% yield with 91% ee (E value = 23) and MPEG-supported 5.