Simultaneous Chirality Sensing of Multiple Amines by 19F NMR.

TitleSimultaneous Chirality Sensing of Multiple Amines by 19F NMR.
Publication TypeJournal Article
Year of Publication2015
AuthorsZhao, Y, Swager, TM
JournalJournal of the American Chemical Society
Keywordsmultiple amine simultaneous chirality sensing F19 NMR, palladium complex chiral pincer ligand selector amine chirality NMR

The rapid detection and differentiation of chiral compds. is important to synthetic, medicinal, and biol. chem. Palladium complexes with chiral pincer ligands have utility in detg. the chirality of various amines. The binding of enantiomeric amines induces distinct 19F NMR shifts of the fluorine atoms appended on the ligand that defines a chiral environment around palladium. Further this method has the ability to evaluate the enantiomeric compn. 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 resoln. of chiral aliph. amines that are difficult to sep. using chiral chromatog. [on SciFinder(R)]