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: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2011
Subjects:
alcohols
carbamates
lipases
kinetic resolution
enatiopure
Organic chemistry
QD241-441
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules16098098
https://doaj.org/article/927f01dd98ae4f7d9ce9372cf247034e
id ftdoajarticles:oai:doaj.org/article:927f01dd98ae4f7d9ce9372cf247034e
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spelling ftdoajarticles:oai:doaj.org/article:927f01dd98ae4f7d9ce9372cf247034e 2023-05-15T13:54:00+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 2011-09-01T00:00:00Z https://doi.org/10.3390/molecules16098098 https://doaj.org/article/927f01dd98ae4f7d9ce9372cf247034e EN eng MDPI AG http://www.mdpi.com/1420-3049/16/9/8098/ https://doaj.org/toc/1420-3049 doi:10.3390/molecules16098098 1420-3049 https://doaj.org/article/927f01dd98ae4f7d9ce9372cf247034e Molecules, Vol 16, Iss 9, Pp 8098-8109 (2011) alcohols carbamates lipases kinetic resolution enatiopure Organic chemistry QD241-441 article 2011 ftdoajarticles https://doi.org/10.3390/molecules16098098 2022-12-31T14:42:16Z 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. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 16 9 8098 8109
institution Open Polar
collection Directory of Open Access Journals: DOAJ Articles
op_collection_id ftdoajarticles
language English
topic alcohols
carbamates
lipases
kinetic resolution
enatiopure
Organic chemistry
QD241-441
spellingShingle alcohols
carbamates
lipases
kinetic resolution
enatiopure
Organic chemistry
QD241-441
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
Organic chemistry
QD241-441
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 Article in Journal/Newspaper
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 MDPI AG
publishDate 2011
url https://doi.org/10.3390/molecules16098098
https://doaj.org/article/927f01dd98ae4f7d9ce9372cf247034e
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Molecules, Vol 16, Iss 9, Pp 8098-8109 (2011)
op_relation http://www.mdpi.com/1420-3049/16/9/8098/
https://doaj.org/toc/1420-3049
doi:10.3390/molecules16098098
1420-3049
https://doaj.org/article/927f01dd98ae4f7d9ce9372cf247034e
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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