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]
Titolo: | Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol | |
Autori: | CASATI, SILVANA MARIA (Primo) SANTANIELLO, ENZO (Secondo) CIUFFREDA, PIERANGELA (Corresponding) | |
Parole Chiave: | lipase-catalyzed benzoylation; platelet-activating-factor; biocatalytic reduction; stereochemical control; chemoenzymatic synthesis; asymmetric reduction; aromatic ketones; yeast reductions; miehei lipase | |
Settore Scientifico Disciplinare: | Settore BIO/10 - Biochimica | |
Data di pubblicazione: | 15-mar-2012 | |
Rivista: | ||
Tipologia: | Article (author) | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tetasy.2012.03.008 | |
Appare nelle tipologie: | 01 - Articolo su periodico |
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