title: Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (-)-Paroxetine.
abstract: A new chemoenzymatic method for the preparation of an intermediate of (-)-Paroxetine is reported. Cyclic anhydrides are used as acylating agents in the lipase-catalyzed esterification of trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine in organic solvents. The best enantioselectivities are obtained with two different lipases from Candida antarctica. These two lipases show opposite stereochemical preference in these processes, so that both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer is an intermediate for the synthesis of (-)-Paroxetine.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: de Gonzalo
authors.forename: Rosario
authors.initials: R
authors.lastname: Brieva
authors.forename: Víctor M
authors.initials: VM
authors.lastname: Sánchez
authors.forename: Miguel
authors.initials: M
authors.lastname: Bayod
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: D000107:Acetylation; D000812:Anhydrides / Q000737:chemistry / Q000378:metabolism*; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D004951:Esterification; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism*; D017374:Paroxetine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D010880:Piperidines / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
chemical_list: C478925:4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine; D000812:Anhydrides; D007202:Indicators and Reagents; D010880:Piperidines; D012997:Solvents; D017374:Paroxetine; D008049:Lipase