MIT

Simultaneous Chirality Sensing of Multiple Amines by 19F NMR.

Title

Simultaneous Chirality Sensing of Multiple Amines by 19F NMR.

Publication Type
Journal Article
Year of Publication
2015
Journal
Journal of the American Chemical Society
Volume
137
Pagination
3221–3224
ISSN
0002-7863
Abstract
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)]