10.1002/chem.201702354
Chemistry - A European Journal
was observed at 4439. Although the products formed in
CDCl3 might not be exactly the same as those formed in
the fluorous solvent, this NMR study demonstrates that
compound (S)-6 reacts with the two enantiomers of
DACH differently which should contribute to the ob-
served enantioselective fluorescent response.
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In conclusion, we have demonstrated that the
BINOL-based aldehyde (S)-6 with four perfluoroalkyl
substituents can be used to conduct highly enantioselec-
tive fluorescent recognition of a chiral diamine in a bi-
phasic fluorous/methanol system with the ef value up to
4.0. This compound can be used to determine the enan-
tiomeric composition of the chiral diamine. The fluo-
rescent recognition in a biphasic system can simplify the
analysis of the screening experiments of chemical reac-
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ACKNOWLEDGMENT
We thank the support of this work by the US National Sci-
ence Foundation (CHE-1565627). Partial supports of this
work from the donors of the Petroleum Research Fund—
administered by the American Chemical Society are also
gratefully acknowledged.
14. Zhang, X., Lippard, S. J. Org. Chem. 2000, 65, 5298-5305.
Keywords: fluorous phase, enantioselective fluorescent
sensing, chiral amine, BINOL, aldehyde
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