The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1,3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e. of 3-(benz-1,3-oxazol-2-yl)cyclopentan-1-ol 6, 2-(benz-1,3-oxazol-2-yl)cyclohexan-l-ol14 and 4-(2-benz-1,3-oxazol-2-yl)cycloheptan-1-ol 21 can be enhanced to 98% using lipase catalyzed resolution.