Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol

Abstract The stereoselective synthesis of ( S )- and ( R )-3-allyloxy-propane-1,2-diol has been accomplished in four steps from ( RS )-3-allyloxy-propane-1,2-diol. Only one intermediate, namely 1-benzoyloxy-3-allyloxy-2-propanone has been prepared by a chemical reaction, that is, pyridinium chlorochromate oxidation of 1-benzoyloxy-3-allyloxypropan-2-ol. All of the remaining reactions (regioselective acylations, asymmetric bioreduction of prochiral ketones, and enzymatic alcoholysis) have been carried out in the presence of biocatalysts.