Hydrolytic resolution of tertiary acetylenic acetate esters with the lipase from Candida cylindracea

Abstract

The kinetic resolution of a series of tertiary acetylenic acetate esters using the lipase from Candida cylindracea has been explored. Compounds 6c and the trifluoromethyl acetate 6e have been resolved with high enantiomeric enrichments. Several other tertiary acetate esters carrying a CF3 group have been investigated which proved inert to enzymatic hydrolysis. From these results and published data, we are able to propose a predictive model for identifying the preferred enantiomer of secondary and tertiary trifluoromethyl acetate esters for this lipase.