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.
Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol / S. Casati, E. Santaniello, P. Ciuffreda. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 23:5(2012 Mar 15), pp. 395-400. [10.1016/j.tetasy.2012.03.008]
Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol
S. CasatiPrimo
;E. SantanielloSecondo
;P. Ciuffreda
2012
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.File | Dimensione | Formato | |
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