Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols

Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation...

Full description

Bibliographic Details
Published in:Synthesis
Main Authors: Maywald, Matthias, Pfaltz, Andreas
Format: Article in Journal/Newspaper
Language:unknown
Published: Georg Thieme 2009
Subjects:
Antarc*
Antarctica
Online Access:http://edoc.unibas.ch/dok/A5253843
https://edoc.unibas.ch/15026/
https://doi.org/10.1055/s-0029-1216997
id ftunivbasel:oai:edoc.unibas.ch:15026
record_format openpolar
spelling ftunivbasel:oai:edoc.unibas.ch:15026 2023-05-15T13:36:10+02:00 Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols Maywald, Matthias Pfaltz, Andreas 2009 http://edoc.unibas.ch/dok/A5253843 https://edoc.unibas.ch/15026/ https://doi.org/10.1055/s-0029-1216997 unknown Georg Thieme Maywald, Matthias and Pfaltz, Andreas. (2009) Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols. Synthesis, 2009 (21). pp. 3654-3660. doi:10.1055/s-0029-1216997 urn:ISSN:0039-7881 urn:ISSN:1437-210X info:eu-repo/semantics/closedAccess Article PeerReviewed 2009 ftunivbasel https://doi.org/10.1055/s-0029-1216997 2023-03-05T06:53:54Z Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation and filtration or distillation, thus avoiding laborious column chromatography, which is a major obstacle for large-scale reactions. This method has been successfully applied to the multigram synthesis of enantiopure pyridyl alcohols. Article in Journal/Newspaper Antarc* Antarctica University of Basel: edoc Synthesis 2009 21 3654 3660
institution Open Polar
collection University of Basel: edoc
op_collection_id ftunivbasel
language unknown
description Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation and filtration or distillation, thus avoiding laborious column chromatography, which is a major obstacle for large-scale reactions. This method has been successfully applied to the multigram synthesis of enantiopure pyridyl alcohols.
format Article in Journal/Newspaper
author Maywald, Matthias
Pfaltz, Andreas
spellingShingle Maywald, Matthias
Pfaltz, Andreas
Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
author_facet Maywald, Matthias
Pfaltz, Andreas
author_sort Maywald, Matthias
title Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
title_short Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
title_full Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
title_fullStr Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
title_full_unstemmed Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols
title_sort chromatography-free enzymatic kinetic resolution of secondary alcohols
publisher Georg Thieme
publishDate 2009
url http://edoc.unibas.ch/dok/A5253843
https://edoc.unibas.ch/15026/
https://doi.org/10.1055/s-0029-1216997
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_relation Maywald, Matthias and Pfaltz, Andreas. (2009) Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols. Synthesis, 2009 (21). pp. 3654-3660.
doi:10.1055/s-0029-1216997
urn:ISSN:0039-7881
urn:ISSN:1437-210X
op_rights info:eu-repo/semantics/closedAccess
op_doi https://doi.org/10.1055/s-0029-1216997
container_title Synthesis
container_volume 2009
container_issue 21
container_start_page 3654
op_container_end_page 3660
_version_ 1766075007923912704

Similar Items