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2005
Alcohols
Q 0870
10- 093
Enantioselective Fluorescent Recognition of Chiral Acids by 3- and 3,3'-Aminomethyl Substituted BINOLs. — The application of enantiopure aminomethyl-substituted BINOL derivatives (I)—(III) is presented in the enantioselective fluorescent recognition of optically active mandelic acid and N-Cbz-phenylglycine. Thus, the fluorescence of derivative (I) is enhanced 30-fold in the presence of (S)-mandelic acid with an
enantiomeric fluorescence difference ratio (ef) of 4.2. Slightly worse results are
achieved with N-Cbz-phenylglycine. On the other side, compound (II) shows a 15-fold
fluorescence enhancement in the presence of N-Cbz-D-phenylglycine with an ef of up
to 5.0. The mono-aminomethylated analogue (III) shows only low fluorescence enhancement with an ef of less than 1.4. These results make compounds (I) and (II) useful
sensors for the recognition of chiral acids in apolar solvents. — (LIN, J.; RAJARAM,
A. R.; PU*, L.; Tetrahedron 60 (2004) 49, 11277-11281; Dep. Chem., Univ. Va.,
Charlottesville, VA 22904, USA; Eng.) — Mischke
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