Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids
Abstract Efficient enantioselective acylation of ( R , S )‐1‐trimethylsilylethanol {( R , S )‐1‐TMSE} with vinyl acetate catalyzed by immobilized lipase from Candida antarctica B (i.e., Novozym 435) was successfully conducted in ionic liquids (ILs). A remarkable enhancement in the initial rate and t...
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crwiley:10.1002/chir.20307 2024-06-23T07:46:53+00:00 Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids Lou, Wen‐Yong Zong, Min‐Hua 2006 http://dx.doi.org/10.1002/chir.20307 http://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20307 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20307 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chirality volume 18, issue 10, page 814-821 ISSN 0899-0042 1520-636X journal-article 2006 crwiley https://doi.org/10.1002/chir.20307 2024-06-06T04:22:58Z Abstract Efficient enantioselective acylation of ( R , S )‐1‐trimethylsilylethanol {( R , S )‐1‐TMSE} with vinyl acetate catalyzed by immobilized lipase from Candida antarctica B (i.e., Novozym 435) was successfully conducted in ionic liquids (ILs). A remarkable enhancement in the initial rate and the enantioselectivity of the acylation was observed by using ILs as the reaction media when compared to the organic solvents tested. Also, the activity, enantioselectivity, and thermostability of Novozym 435 increased with increasing hydrophobicity of ILs. Of the six ILs examined, the IL C 4 MIm·PF 6 gave the fastest initial rate and the highest enantioselectivity, and was consequently chosen as the favorable medium for the reaction. The optimal molar ratio of vinyl acetate to ( R , S )‐1‐TMSE, water activity, and reaction temperature range were 4:1, 0.75, and 40 –50°C, respectively, under which the initial rate and the enantioselectivity ( E value) were 27.6 mM/h and 149, respectively. After a reaction time of 6 h, the ee of the remaining ( S )‐1‐TMSE reached 97.1% at the substrate conversion of 50.7%. Additionally, Novozym 435 was effectively recycled and reused in C 4 MIm·PF 6 for five consecutive runs without substantial lose in activity and enantioselectivity. The preparative scale kinetic resolution of ( R , S )‐1‐TMSE in C 4 MIm·PF 6 is shown to be very promising and useful for the industrial production of enantiopure ( S )‐1‐TMSE. Chirality 2006. © 2006 Wiley‐Liss, Inc. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Chirality 18 10 814 821 |
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Abstract Efficient enantioselective acylation of ( R , S )‐1‐trimethylsilylethanol {( R , S )‐1‐TMSE} with vinyl acetate catalyzed by immobilized lipase from Candida antarctica B (i.e., Novozym 435) was successfully conducted in ionic liquids (ILs). A remarkable enhancement in the initial rate and the enantioselectivity of the acylation was observed by using ILs as the reaction media when compared to the organic solvents tested. Also, the activity, enantioselectivity, and thermostability of Novozym 435 increased with increasing hydrophobicity of ILs. Of the six ILs examined, the IL C 4 MIm·PF 6 gave the fastest initial rate and the highest enantioselectivity, and was consequently chosen as the favorable medium for the reaction. The optimal molar ratio of vinyl acetate to ( R , S )‐1‐TMSE, water activity, and reaction temperature range were 4:1, 0.75, and 40 –50°C, respectively, under which the initial rate and the enantioselectivity ( E value) were 27.6 mM/h and 149, respectively. After a reaction time of 6 h, the ee of the remaining ( S )‐1‐TMSE reached 97.1% at the substrate conversion of 50.7%. Additionally, Novozym 435 was effectively recycled and reused in C 4 MIm·PF 6 for five consecutive runs without substantial lose in activity and enantioselectivity. The preparative scale kinetic resolution of ( R , S )‐1‐TMSE in C 4 MIm·PF 6 is shown to be very promising and useful for the industrial production of enantiopure ( S )‐1‐TMSE. Chirality 2006. © 2006 Wiley‐Liss, Inc. |
format |
Article in Journal/Newspaper |
author |
Lou, Wen‐Yong Zong, Min‐Hua |
spellingShingle |
Lou, Wen‐Yong Zong, Min‐Hua Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
author_facet |
Lou, Wen‐Yong Zong, Min‐Hua |
author_sort |
Lou, Wen‐Yong |
title |
Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
title_short |
Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
title_full |
Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
title_fullStr |
Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
title_full_unstemmed |
Efficient kinetic resolution of ( R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
title_sort |
efficient kinetic resolution of ( r,s)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids |
publisher |
Wiley |
publishDate |
2006 |
url |
http://dx.doi.org/10.1002/chir.20307 http://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20307 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20307 |
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Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chirality volume 18, issue 10, page 814-821 ISSN 0899-0042 1520-636X |
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http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chir.20307 |
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