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A facile chemoenzymatic route to enantiomerically pure 4,5-disubstituted-2-hexenoate derivatives.
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1991
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4,5-Disubstituted-2-hexenoate DerivativesAlcaligenes SpBioorganic ChemistryEngineeringBiochemistryNatural SciencesBiocatalysisVarious NucleophilesOrganic ChemistryStereoselective SynthesisPharmacologyPl 266Synthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
The reaction of 4, 5-epoxy-2-hexenoate 2__- and various nucleophiles in the presenece of BF3.Et20 predominantly gave the (4, 5)-5-hydroxy-4-substituted compounds. Among them, (±)-(4, 5)-anti-5-hydroxy-4-thiophenoxy ester 17 was enantioselectively esterified with acylating reagent in the presence of lipase "PL 266" from Alcaligenes sp. to provide the (4S, 5R)-5-acetoxy ester 20 and the (4R, 5S)-17 quantitatively.