title: Enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes.
abstract: The enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl) phenylcarbamate via lipase-catalyzed transesterification reaction was studied. We investigated several reaction conditions and the carbamate was resolved by Candida antarctica lipase B (CAL-B), leading to the optically pure (R)- and (S)-enantiomers. The enzymatic process showed excellent enantioselectivity (E > 200). (R)- and (S)-tert-butyl 2-(1-hydroxyethyl)phenylcarbamate were easily transformed into the corresponding (R)- and (S)-1-(2-aminophenyl)ethanols.
authors.affiliation: Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, São Paulo, Brazil.
authors.forename: Leandro
authors.initials: L
authors.lastname: Piovan
authors.forename: Monica D
authors.initials: MD
authors.lastname: Pasquini
authors.forename: Leandro H
authors.initials: LH
authors.lastname: Andrade
mesh_terms: D055162:Biocatalysis; D002175:Candida / Q000201:enzymology*; D004951:Esterification; D005656:Fungal Proteins / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D048448:Phenylcarbamates / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013691:Tellurium / Q000737:chemistry*
chemical_list: D005656:Fungal Proteins; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; D048448:Phenylcarbamates; D012997:Solvents; C568733:tert-butyl 2-(1-hydroxyethyl)phenylcarbamate; D008049:Lipase; C431349:lipase B, Candida antarctica; D013691:Tellurium