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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

,  and *
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 alcohols; carbamates; lipases; kinetic resolution; enatiopure
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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