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 (S...

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Published in:Molecules
Main Authors: Piovan, Leandro, Pasquini, Monica D., Andrade, Leandro H.
Format: Text
Language:English
Published: MDPI 2011
Subjects:
Article
Antarc*
Antarctica
Online Access:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264364/
http://www.ncbi.nlm.nih.gov/pubmed/21934647
https://doi.org/10.3390/molecules16098098
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spelling ftpubmed:oai:pubmedcentral.nih.gov:6264364 2023-05-15T13:40:41+02:00 Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes Piovan, Leandro Pasquini, Monica D. Andrade, Leandro H. 2011-09-20 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264364/ http://www.ncbi.nlm.nih.gov/pubmed/21934647 https://doi.org/10.3390/molecules16098098 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264364/ http://www.ncbi.nlm.nih.gov/pubmed/21934647 http://dx.doi.org/10.3390/molecules16098098 © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). CC-BY Article Text 2011 ftpubmed https://doi.org/10.3390/molecules16098098 2018-12-16T01:17:53Z 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 PubMed Central (PMC) Molecules 16 9 8098 8109
institution Open Polar
collection PubMed Central (PMC)
op_collection_id ftpubmed
language English
topic Article
spellingShingle Article
Piovan, Leandro
Pasquini, Monica D.
Andrade, Leandro H.
Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes
topic_facet Article
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 Piovan, Leandro
Pasquini, Monica D.
Andrade, Leandro H.
author_facet Piovan, Leandro
Pasquini, Monica D.
Andrade, Leandro H.
author_sort Piovan, Leandro
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 MDPI
publishDate 2011
url http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264364/
http://www.ncbi.nlm.nih.gov/pubmed/21934647
https://doi.org/10.3390/molecules16098098
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_relation http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264364/
http://www.ncbi.nlm.nih.gov/pubmed/21934647
http://dx.doi.org/10.3390/molecules16098098
op_rights © 2011 by the authors;
licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
op_rightsnorm CC-BY
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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