Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR
Name
chirality sensing manuscript r2.pdf
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896.75 KB
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Adobe PDF
Checksum (MD5)
477bce4ebcd613a9eed0b955d9c4db29
Author(s)
Zhao, Yanchuan
Swager, Timothy M
Date Issued
March 2015
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhao, Yanchuan, and Timothy M. Swager. “Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR.” Journal of the American Chemical Society 137, 9 (February 2015): 3221–3224 © 2015 American Chemical Society
Version
Author's final manuscript
Abstract
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 ¹⁹F 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/jacs.5b00556
