“…Lipasecatalyzed transesterification of the fluorinated allylic alcohols 1 with vinyl acetate in organic medium was superior over the hydrolysis in a phosphate buffer of corresponding acetates 2. The former acetylation gave (S)-(À)-3-acetoxy-2-fluoroalk-1-enes, (S)-(À)-2a-c, of chain lengths C 10 , C 16 and C 18 with 68-89% yield and 92-96% ee, while the remaining (R)-(+)-2-fluoroalk-1-en-3-ols, (R)-(+)-1a-c, were isolated with 54-96% yield and 72-86% ee. Thus, the enantiopreference for the fluorinated allylic alcohols was that predicted by the Kazlauskas rule for the selectivity of serine proteases.…”