Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount
A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%–99% ee and 76%–89% yields. An enantiocomplementarity was establishe...
Published in: | Catalysts |
---|---|
Main Authors: | , , , |
Format: | Text |
Language: | English |
Published: |
Multidisciplinary Digital Publishing Institute
2014
|
Subjects: | |
Online Access: | https://doi.org/10.3390/catal4030215 |
id |
ftmdpi:oai:mdpi.com:/2073-4344/4/3/215/ |
---|---|
record_format |
openpolar |
spelling |
ftmdpi:oai:mdpi.com:/2073-4344/4/3/215/ 2023-08-20T04:00:46+02:00 Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount Nassima Bouzemi Ismahane Grib Zahia Houiene Louisa Aribi-Zouioueche 2014-06-26 application/pdf https://doi.org/10.3390/catal4030215 EN eng Multidisciplinary Digital Publishing Institute https://dx.doi.org/10.3390/catal4030215 https://creativecommons.org/licenses/by/3.0/ Catalysts; Volume 4; Issue 3; Pages: 215-225 deracemisation lipase hydrolysis stereoinversion arylalkylcarbinol Text 2014 ftmdpi https://doi.org/10.3390/catal4030215 2023-07-31T20:38:01Z A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%–99% ee and 76%–89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%–99% ee and 76%–89% yield. Text Antarc* Antarctica MDPI Open Access Publishing Catalysts 4 3 215 225 |
institution |
Open Polar |
collection |
MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
deracemisation lipase hydrolysis stereoinversion arylalkylcarbinol |
spellingShingle |
deracemisation lipase hydrolysis stereoinversion arylalkylcarbinol Nassima Bouzemi Ismahane Grib Zahia Houiene Louisa Aribi-Zouioueche Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
topic_facet |
deracemisation lipase hydrolysis stereoinversion arylalkylcarbinol |
description |
A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%–99% ee and 76%–89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%–99% ee and 76%–89% yield. |
format |
Text |
author |
Nassima Bouzemi Ismahane Grib Zahia Houiene Louisa Aribi-Zouioueche |
author_facet |
Nassima Bouzemi Ismahane Grib Zahia Houiene Louisa Aribi-Zouioueche |
author_sort |
Nassima Bouzemi |
title |
Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
title_short |
Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
title_full |
Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
title_fullStr |
Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
title_full_unstemmed |
Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount |
title_sort |
enantiocomplementary preparation of (s)- and (r)-arylalkylcarbinols by lipase-catalysed resolution and mitsunobu inversion: impact of lipase amount |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2014 |
url |
https://doi.org/10.3390/catal4030215 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts; Volume 4; Issue 3; Pages: 215-225 |
op_relation |
https://dx.doi.org/10.3390/catal4030215 |
op_rights |
https://creativecommons.org/licenses/by/3.0/ |
op_doi |
https://doi.org/10.3390/catal4030215 |
container_title |
Catalysts |
container_volume |
4 |
container_issue |
3 |
container_start_page |
215 |
op_container_end_page |
225 |
_version_ |
1774720202548707328 |