Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl]ethers of 3-chloro-1,2-propanediol

Article abstract of DOI:10.1016/S0957-4166(00)80140-8

The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products was verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)-epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.