Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 27, Pages 9494-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja903371d
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Premier International Research Center Initiative (WPI Initiative)
- MEXT, Japan
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Until now NMR spectroscopic detection of guest chirality using an achiral host has not been possible in the absence of a chiral medium or auxiliary since chiral discrimination is principally based on chiral discrimination by host and/or diastereomeric host-guest complex formation. In this paper, we demonstrate that an achiral. oxoporphyrinogen works as a host capable of Signaling chiral information of alpha-hydroxycarboxylic acids in H-1 NMR spectroscopy. In particular, enantiomeric excess (ee) can be determined by observing the splitting of H-1 NMR resonances of the achiral host. This differs from the case of chiral hosts (shift reagents) where % ee is generally determined from the ratio of peak areas due to diastereomeric host-guest complexes. UV/vis, CD, FT-IR, and NMR spectroscopic investigations suggest that the unusual phenomenon reported here is based on formation of a complex with 1:2 stoichiometry in concert with a protonation-driven tautomerization of the host.
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