Simultaneous chirality sensing of multiple amines by (19)F NMR.
The rapid detection and differentiation of chiral compounds is important to synthetic, medicinal, and biological chemistry. Palladium complexes with chiral pincer ligands are demonstrated to have utility in determining the chirality of various amines. The binding of enantiomeric amines induces distinct (19)F NMR shifts of the fluorine atoms appended on the ligand that defines a chiral environment around palladium. It is further demonstrated that this method has the ability to evaluate the enantiomeric composition and discriminate between enantiomers with chiral centers several carbons away from the binding site. The wide detection window provided by optimized chiral chemosensors allows the simultaneous identification of as many as 12 chiral amines. The extraordinary discriminating ability of this method is demonstrated by the resolution of chiral aliphatic amines that are difficult to separate using chiral chromatography.
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Yanchuan
Y
Zhao
Timothy M
TM
Swager
D000588:Amines / Q000032:analysis* / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010165:Palladium / Q000737:chemistry; D010627:Phenethylamines / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D008024:Ligands; D010627:Phenethylamines; D005461:Fluorine; D010165:Palladium; C033198:1-phenethylamine