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

摘要

[GRAPHICS]The long-chain aliphatic-group-substituted mandelic acid 3c, which is soluble only in THF and insoluble in water and many polaronpolar 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.