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
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
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