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Stereospecific Ring Opening at the Benzylic Carbon of Phenyloxirane Derivatives by Alcohols
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1991
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Benzyl AlcoholEngineeringHeterocyclicAlkene MetathesisOrganic ChemistryBenzylic CarbonChemistryBenzylic PositionHeterocycle ChemistryStereoselective SynthesisPure Phenyl-substituted OxiranesStereospecific Ring OpeningBiomolecular EngineeringPhenyloxirane Derivatives
Optically pure phenyl-substituted oxiranes underwent stereospecific ring opening at the benzylic position by benzyl alcohol and methanol with complete inversion under the catalysis of organotin phosphate condensates. With recourse to this reaction, a novel procedure for (S)-phenyloxirane was achieved from the readily available R counterpart via (S)-2-benzyloxy-2-phenylethanol.