A1 Journal article – refereed
Lipase-catalyzed asymmetric acylation in the chemoenzymatic synthesis of furan-based alcohols

List of Authors: Hara P, Turcu MC, Sundell R, Tosa M, Paizs C, Irimie FD, Kanerva LT
Publication year: 2013
Journal: Tetrahedron: Asymmetry
Journal name in source: TETRAHEDRON-ASYMMETRY
Number in series: 2-3
Volume number: 24
Issue number: 2-3
Number of pages: 9
ISSN: 0957-4166

Eight racemic 1-(furan-2-yl)ethanols were prepared from the corresponding carbonyl compounds for enantioselective acylation studies, and seven of them were used in preparative-scale kinetic resolutions with Candida antarctica lipase B (Novozym 435) and vinyl acetate in dried diisopropyl ether. Mechanism-based competition between the (R)-acetate (enzymatic acylation product), vinyl acetate (added acylating reagent), and acetic acid (enzymatic hydrolysis product) toward CAL-B, together with the residual water of the lipase were shown to be potential reasons for side reactions, which affected the course of the kinetic resolution of 1-[5-(2-chlorophenyl) and (4-bromophenyl)furan-2-yl]ethanols. Clear effects were not observed with the other alcoholic substrates. Alcoholysis of the enantiomerically enriched (R)-acetates with methanol and CAL-B in diisopropyl ether was shown to be a potential method for the deprotection of the (R)-acetates and the formation of (R)-alcohols. (C) 2012 Elsevier Ltd. All rights reserved.

Internal Authors/Editors

Research Areas

Downloadable publication

This is an electronic reprint of the original article.
This reprint may differ from the original in pagination and typographic detail. Please cite the original version.

Last updated on 2019-21-08 at 23:30