Molecules 2011, 16(9), 8098-8109; doi:10.3390/molecules16098098
Article

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

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.
Received: 19 August 2011; in revised form: 14 September 2011 / Accepted: 15 September 2011 / Published: 20 September 2011
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
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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

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MDPI and ACS Style

Piovan, L.; Pasquini, M.D.; Andrade, L.H. Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes. Molecules 2011, 16, 8098-8109.

AMA Style

Piovan L, Pasquini MD, Andrade LH. Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes. Molecules. 2011; 16(9):8098-8109.

Chicago/Turabian Style

Piovan, Leandro; Pasquini, Monica D.; Andrade, Leandro H. 2011. "Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes." Molecules 16, no. 9: 8098-8109.

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