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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Bibliographic Details
Published in:Canadian Journal of Chemistry
Main Authors: Gedey, Szilvia, Liljeblad, Arto, Lázár, László, Fülöp, Ferenc, Kanerva, Liisa T
Format: Article in Journal/Newspaper
Language:English
Published: Canadian Science Publishing 2002
Subjects:
Organic Chemistry
General Chemistry
Catalysis
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1139/v02-015
http://www.nrcresearchpress.com/doi/pdf/10.1139/v02-015
Description
Summary: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.

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