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...

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Bibliographic Details
Published in:Organic letters 2005-08, Vol.7 (16), p.3441-3444
Main Authors: Li, Zi-Bo, Lin, Jing, Qin, Ying-Chuan, Pu, Lin
Format: Article
Language:English
Subjects:
Catalysis
Mandelic Acids - chemical synthesis
Mandelic Acids - chemistry
Solvents
Spectrometry, Fluorescence
Stereoisomerism
Water
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0510163