Enantioselective fluorescent recognition of a soluble "supported" chiral acid: toward a new method for chiral catalyst screening.
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]
Li
Zi-Bo
ZB
Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.
Lin
Jing
J
Qin
Ying-Chuan
YC
Pu
Lin
L
D002384:Catalysis; D008333:Mandelic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D014867:Water
D008333:Mandelic Acids; D012997:Solvents; D014867:Water; C037938:mandelic acid