title: Novel lipase-catalysed enantioselective deacetylation of (+/-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine.
abstract: (+/-)-5-Acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine has been synthesised by a highly diastereoselective [3+2] cycloaddition reaction between alpha-(4-fluorophenyl)-N-phenylnitrone and vinyl acetate in good yield. Candida rugosa lipase catalyses the deacetylation of this (+/-)-5-acetoxyisoxazolidine in a highly enantioselective fashion in diisopropyl ether containing n-butanol affording (-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine in 43% yield and >99% ee.
authors.affiliation: Department of Chemistry, University of Delhi, -110 007, Delhi, India.
authors.forename: S
authors.initials: S
authors.lastname: Mukherjee
authors.forename: A K
authors.initials: AK
authors.lastname: Prasad
authors.forename: V S
authors.initials: VS
authors.lastname: Parmar
authors.forename: O W
authors.initials: OW
authors.lastname: Howarth
mesh_terms: D000107:Acetylation; D000818:Animals; D002384:Catalysis; D007555:Isoxazoles / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D008968:Molecular Conformation; D013552:Swine
chemical_list: C435623:5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine; D007555:Isoxazoles; D008049:Lipase