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Study for the determination of the absolute configuration
Journal of Fluorine Chemistry 84 (1997) 19–23
0022-1139/97/$17.00 q 1997 Elsevier Science S.A. All rights reserved
PII S0022- 1139 (97)00026 -2
Journal: FLUOR (Journal of Fluorine Chemistry) Article: 3601
Study for the determination of the absolute configuration of
fluoromethylated secondary alcohols by the modified Mosher method
Ling Xiao
a
, Takashi Yamazaki
a
, Tomoya Kitazume
a,U
, Tetsuo Yonezawa
b
,
Yoshitake Sakamoto
b
, Kouji Nogawa
b
a
Department of Bioengineering, Tokyo Institute of Technology, Nagatsuta, Midori-ku Yokohama 226, Japan
b
Department of Research and Development, Morita Chemical Industries Co. Ltd., Higasi-mikuni, Yadogawa-ku, Osaka 532, Japan
Received 6 September 1996; accepted 15 February 1997
Abstract
Application of the modified Mosher method using high-field FT
1
H NMR to the 2-methoxy-2-phenyl-2-trifluoromethyl acetic acid (MTPA)
derivatives of fluorinated secondary alcohols indicates that this method may be generally used to determine the absolute configurations of
these materials. q 1997 Elsevier Science S.A.
Keywords: Fluorinated secondary alcohols; Absolute configuration
Fig. 2. Model used to determine the absolute configurations of secondary
alcohols.
Fig. 1. MTPA plane of an MTPA ester. H
A,B,C
and H
X,Y,Z
are on the left and
right sides of the plane respectively.
1. Introduction
One objective of research in fluorine chemistry, required
to support applications in fluorine analogs of bioactive [1]
and/or functionalized materials [2], is the development of
methodology suitable for determination of the absolute con-
figuration. There are a few physical methods, e.g. the exciton
chirality method [3] and X-ray crystallography, however
they have some limitations. Recently, in hydrocarbon chem-
istry, Kakisawa and coworkers have reported that a modifi-
cation of Mosher’s method is useful to elucidate the absolute
configuration of secondary alcohols [4].
Accordingly, we have devoted our attention to application
of the modified Mosher method
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