A VERSATILE APPROACH TO OPTICALLY-ACTIVE PRIMARY 2-FLUORO-2-PHENYLALKANOLS THROUGH LIPASE-CATALYZED TRANSFORMATIONS

Authors
GOJ O BURCHARDT A HAUFE G
Citation
O. Goj et al., A VERSATILE APPROACH TO OPTICALLY-ACTIVE PRIMARY 2-FLUORO-2-PHENYLALKANOLS THROUGH LIPASE-CATALYZED TRANSFORMATIONS, Tetrahedron : asymmetry, 8(3), 1997, pp. 399-408
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
3
Year of publication
1997
Pages
399 - 408
Database
ISI
SICI code
0957-4166(1997)8:3<399:AVATOP>2.0.ZU;2-H
Abstract
Kinetic resolutions of (+/-)-1-acetoxy-2-fluoro-2-phenylalkanes 1 by e nzymatic hydrolysis and of (+/-)-2-fluoro-2-phenylpropanol 2a by lipas e-catalyzed acetylation are described for the first time. Hydrolysis o f (+/-)-1 with lipase Amano PS (Pseudomonas cepacia) provided both the optically active acetates (-)-1 and the corresponding primary alcohol s (-)-2 with high enantiomeric excess. (R)-enantiopreference was obser ved for the acetylation of (+/-)-2-fluoro-2-phenylpropanol 2a which oc curred with higher enantioselectivity and faster conversion compared t o the unfluorinated parent compound (+/-)-2-phenylpropanol 3. (C) 1997 Elsevier Science Ltd. All rights reserved.