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Org Lett. 2005 Aug 4;7(16):3441-4.

Enantioselective fluorescent recognition of a soluble "supported" chiral acid: toward a new method for chiral catalyst screening.

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Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.


The long-chain aliphatic-group-substituted mandelic acid 3c, which is soluble only in THF and insoluble in water and many polar/nonpolar organic solvents, has been synthesized. This unique solubility allows 3c to be easily isolated from reaction mixtures and makes it potentially useful for catalyst screening. The fluorescent sensors (R)- and (S)-1 can be used to determine the ees of various samples of 3c generated from a series of catalyst screening experiments. The fluorescence measurements correlate well with the conventional HPLC-chiral column analysis. This work demonstrates that the enantioselective fluorescent recognition of organic substrates can lead to a fundamentally new method for chiral catalyst screening. [reaction: see text].

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