Abstract The transesterification of 2-substituted-1, 4-butanediols 1a, 2a and 3a with vinyl acetate catalyzed by the Pseudomonas cepacia lipase in organic solvents affords preferentially the 1-acetate, the highest regioselectivity having been found for the epoxydiol 3a, which is enantioselectively resolved [86% ee for the unreacted (S)-(−)-3a].