Racemic cis-and trans-2-aminocyclohexane-1-methanol and cis-and trans-2-amino-4- cyclohexene-1-methanol were resolved via lipase-catalysed O-acylation of their Z derivatives, using vinyl butyrate in different ether solvents. In accordance with the empirical rule, most of the screened lipases preferred the 1S enantiomer.