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enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes酶动力学分辨率叔丁基2 -(1-hydroxyethyl)phenylcarbamate,手性的关键中间organoselenanes organotelluranes.pdfVIP

enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes酶动力学分辨率叔丁基2 -(1-hydroxyethyl)phenylcarbamate,手性的关键中间organoselenanes organotelluranes.pdf

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enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes酶动力学分辨率叔丁基2 -(1-hydroxyethyl)phenylcarbamate,手性的关键中间organoselenanes organotelluranes

Molecules 2011, 16, 8098-8109; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes Leandro Piovan, Monica D. Pasquini and Leandro H. Andrade * Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, São Paulo, Brazil * Author to whom correspondence should be addressed; E-Mail: leandroh@iq.usp.br; Tel./Fax: +55-11-3091-2287. Received: 19 August 2011; in revised form: 14 September 2011 / Accepted: 15 September 2011 / Published: 20 September 2011 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. Keywords: alcohols; carbamates; lipases; kinetic resolution; enatiopure 1. Introduction Selenium- and tellurium-containing compounds have drawn the attention of the scientific community due to their biological prop

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