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

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 (...

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Published in:Molecules
Main Authors: Leandro Piovan, Monica D. Pasquini, Leandro H. Andrade
Format: Text
Language:English
Published: Molecular Diversity Preservation International 2011
Subjects:
alcohols
carbamates
lipases
kinetic resolution
enatiopure
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules16098098
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spelling ftmdpi:oai:mdpi.com:/1420-3049/16/9/8098/ 2023-08-20T04:02:31+02:00 Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes Leandro Piovan Monica D. Pasquini Leandro H. Andrade agris 2011-09-20 application/pdf https://doi.org/10.3390/molecules16098098 EN eng Molecular Diversity Preservation International https://dx.doi.org/10.3390/molecules16098098 https://creativecommons.org/licenses/by-nc-sa/3.0/ Molecules; Volume 16; Issue 9; Pages: 8098-8109 alcohols carbamates lipases kinetic resolution enatiopure Text 2011 ftmdpi https://doi.org/10.3390/molecules16098098 2023-07-31T20:27:17Z 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. Text Antarc* Antarctica MDPI Open Access Publishing Molecules 16 9 8098 8109
institution Open Polar
collection MDPI Open Access Publishing
op_collection_id ftmdpi
language English
topic alcohols
carbamates
lipases
kinetic resolution
enatiopure
spellingShingle alcohols
carbamates
lipases
kinetic resolution
enatiopure
Leandro Piovan
Monica D. Pasquini
Leandro H. Andrade
Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
topic_facet alcohols
carbamates
lipases
kinetic resolution
enatiopure
description 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.
format Text
author Leandro Piovan
Monica D. Pasquini
Leandro H. Andrade
author_facet Leandro Piovan
Monica D. Pasquini
Leandro H. Andrade
author_sort Leandro Piovan
title Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
title_short Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
title_full Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
title_fullStr Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
title_full_unstemmed Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
title_sort enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes
publisher Molecular Diversity Preservation International
publishDate 2011
url https://doi.org/10.3390/molecules16098098
op_coverage agris
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Molecules; Volume 16; Issue 9; Pages: 8098-8109
op_relation https://dx.doi.org/10.3390/molecules16098098
op_rights https://creativecommons.org/licenses/by-nc-sa/3.0/
op_doi https://doi.org/10.3390/molecules16098098
container_title Molecules
container_volume 16
container_issue 9
container_start_page 8098
op_container_end_page 8109
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