Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum
Abstract Kinetic resolution of some chiral secondary alcohols [2‐octanol, 1‐phenylethanol, and 1‐(2‐naphthyl)ethanol] with high enantioselectivity ( E >300) was achieved by direct esterification with FFA catalyzed by immobilized Candida antarctica B lipase. The reaction equilibrium was shifted to...
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crwiley:10.1007/s11746-003-0755-4 2024-06-02T07:57:57+00:00 Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum Irimescu, Roxana Saito, Takao Kato, Katsuya 2003 http://dx.doi.org/10.1007/s11746-003-0755-4 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-003-0755-4 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-003-0755-4 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 80, issue 7, page 659-663 ISSN 0003-021X 1558-9331 journal-article 2003 crwiley https://doi.org/10.1007/s11746-003-0755-4 2024-05-03T10:48:00Z Abstract Kinetic resolution of some chiral secondary alcohols [2‐octanol, 1‐phenylethanol, and 1‐(2‐naphthyl)ethanol] with high enantioselectivity ( E >300) was achieved by direct esterification with FFA catalyzed by immobilized Candida antarctica B lipase. The reaction equilibrium was shifted toward the synthetic side by the removal of the water formed under vacuum. Esterification of rac ‐2‐octanol at an alcohol/FFA molar ratio of 2∶1 was used as a model reaction. The chain length of FFA and their structure influenced the reaction rate but did not have a measureable effect on E . The best acyl donor was decanoic acid: >47% conversion at 4 h with virtually perfect E . Temperature did not affect E in the range studied (15–45°C), but temperatures at the higher end afforded improved reaction rates. The reaction rates and E were compared for three different acyl donors. The initial reaction rate increased in the following order: ethyl laurate < lauric acid < vinyl acetate. E was high ( E >300) for all acyl donors. Racemic 1‐phenylethanol and 1‐(2‐naphthyl)ethanol were also resolved by direct esterification with decanoic acid in short times (3 and 4 h, respectively) with E >300 and excellent conversions. Preparative‐scale kinetic resolution of 2‐octanol was also performed. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 80 7 659 663 |
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English |
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Abstract Kinetic resolution of some chiral secondary alcohols [2‐octanol, 1‐phenylethanol, and 1‐(2‐naphthyl)ethanol] with high enantioselectivity ( E >300) was achieved by direct esterification with FFA catalyzed by immobilized Candida antarctica B lipase. The reaction equilibrium was shifted toward the synthetic side by the removal of the water formed under vacuum. Esterification of rac ‐2‐octanol at an alcohol/FFA molar ratio of 2∶1 was used as a model reaction. The chain length of FFA and their structure influenced the reaction rate but did not have a measureable effect on E . The best acyl donor was decanoic acid: >47% conversion at 4 h with virtually perfect E . Temperature did not affect E in the range studied (15–45°C), but temperatures at the higher end afforded improved reaction rates. The reaction rates and E were compared for three different acyl donors. The initial reaction rate increased in the following order: ethyl laurate < lauric acid < vinyl acetate. E was high ( E >300) for all acyl donors. Racemic 1‐phenylethanol and 1‐(2‐naphthyl)ethanol were also resolved by direct esterification with decanoic acid in short times (3 and 4 h, respectively) with E >300 and excellent conversions. Preparative‐scale kinetic resolution of 2‐octanol was also performed. |
format |
Article in Journal/Newspaper |
author |
Irimescu, Roxana Saito, Takao Kato, Katsuya |
spellingShingle |
Irimescu, Roxana Saito, Takao Kato, Katsuya Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
author_facet |
Irimescu, Roxana Saito, Takao Kato, Katsuya |
author_sort |
Irimescu, Roxana |
title |
Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
title_short |
Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
title_full |
Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
title_fullStr |
Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
title_full_unstemmed |
Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum |
title_sort |
enzymatic kinetic resolution of secondary alcohols by esterification with fa under vacuum |
publisher |
Wiley |
publishDate |
2003 |
url |
http://dx.doi.org/10.1007/s11746-003-0755-4 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-003-0755-4 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-003-0755-4 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 80, issue 7, page 659-663 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-003-0755-4 |
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Journal of the American Oil Chemists' Society |
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80 |
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7 |
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659 |
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1800741187552804864 |