Enantioselective fluorescent recognition of a soluble supported chiral acid: Toward a new method for chiral catalyst screening

[GRAPHICS] 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 en anti oselective fluorescent recognition of organic substrates can lead to a fundamentally new method for chiral catalyst screening.