Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols
Abstract Candida antarctica Lipase B (CALB) catalyzed the highly enantioselective acetylation of 1,3‐ anti ‐diol monoesters which have been obtained through a zirconium‐catalyzed aldol‐Tishchenko reaction. The product 1,3‐ anti ‐diol diesters were formed in yields close to 50 % and >98 % ee . Sep...
Published in: | European Journal of Organic Chemistry |
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crwiley:10.1002/ejoc.200700096 2024-06-02T07:57:33+00:00 Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols Jakob, Florian Schneider, Christoph 2007 http://dx.doi.org/10.1002/ejoc.200700096 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200700096 https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200700096 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Organic Chemistry volume 2007, issue 18, page 2958-2963 ISSN 1434-193X 1099-0690 journal-article 2007 crwiley https://doi.org/10.1002/ejoc.200700096 2024-05-03T11:20:12Z Abstract Candida antarctica Lipase B (CALB) catalyzed the highly enantioselective acetylation of 1,3‐ anti ‐diol monoesters which have been obtained through a zirconium‐catalyzed aldol‐Tishchenko reaction. The product 1,3‐ anti ‐diol diesters were formed in yields close to 50 % and >98 % ee . Separation from the unreactive enantiomers and subsequent hydrolysis furnished both enantiomers of unsymmetrically substituted 1,3‐ anti ‐diols in high optical purities. Alternatively, the kinetic resolution process can be performed on the free 1,3‐ anti ‐diols even more rapidly with equally good results. A slow acyl migration during the reaction slightly deteriorated the enantiomeric excess of the unreactive enantiomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Organic Chemistry 2007 18 2958 2963 |
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Wiley Online Library |
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crwiley |
language |
English |
description |
Abstract Candida antarctica Lipase B (CALB) catalyzed the highly enantioselective acetylation of 1,3‐ anti ‐diol monoesters which have been obtained through a zirconium‐catalyzed aldol‐Tishchenko reaction. The product 1,3‐ anti ‐diol diesters were formed in yields close to 50 % and >98 % ee . Separation from the unreactive enantiomers and subsequent hydrolysis furnished both enantiomers of unsymmetrically substituted 1,3‐ anti ‐diols in high optical purities. Alternatively, the kinetic resolution process can be performed on the free 1,3‐ anti ‐diols even more rapidly with equally good results. A slow acyl migration during the reaction slightly deteriorated the enantiomeric excess of the unreactive enantiomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) |
format |
Article in Journal/Newspaper |
author |
Jakob, Florian Schneider, Christoph |
spellingShingle |
Jakob, Florian Schneider, Christoph Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
author_facet |
Jakob, Florian Schneider, Christoph |
author_sort |
Jakob, Florian |
title |
Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
title_short |
Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
title_full |
Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
title_fullStr |
Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
title_full_unstemmed |
Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters – Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols |
title_sort |
enzyme‐catalyzed kinetic resolution of 1,3‐anti‐diol monoesters – efficient preparation of enantiomerically highly enriched and unsymmetrically substituted 1,3‐anti‐diols |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1002/ejoc.200700096 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200700096 https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200700096 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Organic Chemistry volume 2007, issue 18, page 2958-2963 ISSN 1434-193X 1099-0690 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejoc.200700096 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2007 |
container_issue |
18 |
container_start_page |
2958 |
op_container_end_page |
2963 |
_version_ |
1800740718809972736 |