PPL catalyzed desymmetrization of 2-phenyl-1, 3-propanediol (3) was the key step in the chemoenzymatic synthesis of both enantiomers of 2-phenyl-3-hydroxypropylcarbamate (2). Unsuccessful attempts at enzyme catalyzed (PPL, Novo SP435) transcarbamoylation, aminolysis and ammonolysis are also described.