Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes.docVIP

Molecules 2011, 16, 8098-8109; doi:10.3390/moleculeOPEN 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 S?o Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, S?o 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 properties [1-4]. Notwithstanding the intense activity in the field of selenium and tellurium chemistry over the last three decades, organometallic reagents are commonly employed on the preparation of organo-selenium and -tellurium compounds. Moreover, hypervalent organoselenium(IV) compounds (organoselenanes) and organotellurium(IV) compounds (organotelluranes) have been investigated as cysteine protease [5-8], protein tyrosine phosphatase [9] and poliovirus 3C protein