6533b861fe1ef96bd12c5aad

RESEARCH PRODUCT

Pig liver esterase (PLE)-mediated resolution of N-substituted 4-benzoyloxy-3-carbomethoxypiperidines: A convenient preparation of 4-hydroxy- and 4-benzoyloxy-3-carbomethoxypiperidines in enantiomerically pure form

Marinella RobertiCarlo BertucciStefania GrimaudoManlio TolomeoRiccardo RondaninRiccardo BaruchelloDaniele SimoniR. FerroniVincenza AndrisanoFrancesco Paolo InvidiataValerio Bertolasi

subject

chemistry.chemical_classificationResolution (mass spectrometry)StereochemistryOrganic ChemistryEnantioselective synthesisEsteraseCatalysisInorganic ChemistryHydrolysisEnzymechemistryOrganic chemistryPhysical and Theoretical ChemistryPig liver

description

Abstract Pig liver esterase (PLE) afforded smooth chemical resolution of racemic N -substituted 4-(benzoyloxy)-3-carbomethoxypiperidines. The enzyme showed good chemo- and enantioselective properties, thus allowing discrimination between the carbomethoxy and benzoate ester groups, the latter being more easily hydrolyzed. The proposed methodology also represents a practical means for the procurement of N -substituted 4-hydroxy-3-carbomethoxypiperidines in enantiomerically pure form.

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