Abstract The generation of optically active glycerol derivatives via enzymatic ester hydrolysis of prochiral 1, 3-diacyl derivatives of 2-O-allyl protected glycerol has been investigated. Lipase M-AP, under optimum conditions, afforded asymmetric inductions of 94–96% ee. The obtained (R)-monoacyl derivative was converted to (S)-configurated tosylglycerol compounds.