Enantioselective recognition of carboxylates: a receptor derived from alpha-aminoxy acids functions as a chiral shift reagent for carboxylic acids |
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Authors: | Yang Dan Li Xiang Fan Yun-Fei Zhang Dan-Wei |
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Institution: | Department of Chemistry, Fudan University, Shanghai, China, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China. |
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Abstract: | Enantioselective recognition of carboxylates has important implications in asymmetric synthesis and drug discovery. We have prepared a novel C2-symmetric receptor 1 from alpha-aminoxy acids in a high overall yield. A series of chiral recognition studies indicate that receptor 1 not only can bind to carboxylate ions tightly but also has a good ability to recognize enantiomers of a broad variety of carboxylic acids in the 1H NMR spectra. Thus, the receptor 1 can be used as a chiral shift reagent for the determination of enantiomeric purities of chiral carboxylic acids by 1H NMR directly and rapidly. |
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