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

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.

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(R)-1-Benzoyloxy-3-allyloxypropan-2-olC13H16O4ee 44%[α]D20=-1.3 (c 1, CHCl3)Source of chirality: Baker’s yeast asymmetric bioreductionAbsolute configuration: (R)

(R)-1-Acetoxy-3-allyloxypropan-2-olC8H14O4ee >98%[α]D20=+1.4 (c 1, CHCl3)Source of chirality: Baker’s yeast asymmetric bioreductionAbsolute configuration: (R)

(S)-3-Allyloxy-propane-1,2-diolC6H12O3ee >98%[α]D20=-7.2 (c 1, CHCl3)Source of chirality: Baker’s yeast asymmetric bioreductionAbsolute configuration: (S)