The lipase-catalyzed kinetic resolutions of 2-benzyloxy- and 2-silyloxy-1-propanols have been investigated. Efficient modification of the substrate structure with the dimethylphenylsilyl protecting group and the use of lipase PS-D immobilized on diatomaceous earth were found to enhance the enantioselectivity and reactivity up to E = 240 at 0 degrees C.