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