New macrocyclic compound as chiral shift reagent for carboxylic acids.
[structure: see text] We have prepared a novel chiral macrocyclic compound 3 from a C2-symmetric aminonaphthol in a high yield. Enantiomeric acids have large nonequivalent chemical shifts (up to 0.80 ppm) in the presence of 3 in 1H NMR (500 MHz) spectra. Quantitative analyses of a series of mandelic acids with different enantiomeric purities show that host 3 is an excellent chemical shift reagent for chiral carboxylic acids.
Ma
Fengnian
F
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Ai
Lin
L
Shen
Xiumin
X
Zhang
Cong
C
D002264:Carboxylic Acids / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents; D013237:Stereoisomerism
D002264:Carboxylic Acids; D047028:Macrocyclic Compounds; D012997:Solvents