Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters
The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential r...
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crcansciencepubl:10.1139/v02-015 2023-12-17T10:21:05+01:00 Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters Gedey, Szilvia Liljeblad, Arto Lázár, László Fülöp, Ferenc Kanerva, Liisa T 2002 http://dx.doi.org/10.1139/v02-015 http://www.nrcresearchpress.com/doi/pdf/10.1139/v02-015 en eng Canadian Science Publishing http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining Canadian Journal of Chemistry volume 80, issue 6, page 565-570 ISSN 0008-4042 1480-3291 Organic Chemistry General Chemistry Catalysis journal-article 2002 crcansciencepubl https://doi.org/10.1139/v02-015 2023-11-19T13:38:48Z The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method. Key words: lipase, interesterification, acylation, alcoholysis, resolution, β-amino esters. Article in Journal/Newspaper Antarc* Antarctica Canadian Science Publishing (via Crossref) Canadian Journal of Chemistry 80 6 565 570 |
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Open Polar |
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Canadian Science Publishing (via Crossref) |
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crcansciencepubl |
language |
English |
topic |
Organic Chemistry General Chemistry Catalysis |
spellingShingle |
Organic Chemistry General Chemistry Catalysis Gedey, Szilvia Liljeblad, Arto Lázár, László Fülöp, Ferenc Kanerva, Liisa T Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
topic_facet |
Organic Chemistry General Chemistry Catalysis |
description |
The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method. Key words: lipase, interesterification, acylation, alcoholysis, resolution, β-amino esters. |
format |
Article in Journal/Newspaper |
author |
Gedey, Szilvia Liljeblad, Arto Lázár, László Fülöp, Ferenc Kanerva, Liisa T |
author_facet |
Gedey, Szilvia Liljeblad, Arto Lázár, László Fülöp, Ferenc Kanerva, Liisa T |
author_sort |
Gedey, Szilvia |
title |
Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
title_short |
Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
title_full |
Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
title_fullStr |
Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
title_full_unstemmed |
Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters |
title_sort |
structural effects on chemo- and enantioselectivity of candida antarctica lipase b - resolution of β-amino esters |
publisher |
Canadian Science Publishing |
publishDate |
2002 |
url |
http://dx.doi.org/10.1139/v02-015 http://www.nrcresearchpress.com/doi/pdf/10.1139/v02-015 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Canadian Journal of Chemistry volume 80, issue 6, page 565-570 ISSN 0008-4042 1480-3291 |
op_rights |
http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining |
op_doi |
https://doi.org/10.1139/v02-015 |
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Canadian Journal of Chemistry |
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80 |
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6 |
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565 |
op_container_end_page |
570 |
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1785529459221200896 |