Enantioselective recognition of carboxylates: a receptor derived from alpha-aminoxy acids functions as a chiral shift reagent for carboxylic acids.
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.
Yang
Dan
D
Department of Chemistry, Fudan University, Shanghai, China, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Li
Xiang
X
Fan
Yun-Fei
YF
Zhang
Dan-Wei
DW
D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000032:analysis / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008333:Mandelic Acids / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D008333:Mandelic Acids; C037938:mandelic acid