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Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis

Author:
Forró, Enikő, Galla, Zsolt, Fülöp, Ferenc
Source:
Journal of Molecular Catalysis. B, Enzymatic 2013 v.98 pp. 92-97
ISSN:
1381-1177
Subject:
Pseudozyma antarctica, acetates, acylation, catalysts, catalytic activity, hydrolysis
Abstract:
The ester function of ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate [(±)-1] and ethyl (±)-5-hydroxycyclopent-1-enecarboxylate [(±)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E>200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30°C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee=90%) and 5-hydroxycyclopent-1-enecarboxylic acid (ee=47%) were prepared through de novo CAL-B-catalyzed hydrolysis of (±)-1 and (±)-2 with added H2O in t-BuOMe at 30°C.
Agid:
855367