Journal
CHIRALITY
Volume 20, Issue 5, Pages 691-723Publisher
WILEY
DOI: 10.1002/chir.20478
Keywords
absolute configuration; X-ray crystallography; internal reference; chiral X-ray reference reagents (CXR); camphorsultam dichlorophthalic acid (CSDP acid); H-1 NMR anisotropy; chiral H-1 NMR anisotropy reagents (CAR); 2-methoxy-2-(1-naphthyl)propionic acid; M alpha NP acid; diastereomers; HPLC separation on silica gel
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To determine the absolute configurations of chiral compounds, many spectroscopic and diffraction methods have been developed. Among them, X-ray crystallographic Bijvoet method, CD exciton chirality method, and the combination of vibrational circular dichroism and quantum mechanical calculations are of nonempirical nature. On the other hand, X-ray crystallography using a chiral internal reference, and H-1 NMR spectroscopy using chiral anisotropy reagents are relative and/or empirical methods. In addition to absolute configurational determinations, preparations of enantiopure compounds are strongly desired. As chiral reagents useful for both the preparation of enantiopure compounds by HPLC separation and the simultaneous determination of their absolute configurations, we have developed camphorsultam dichlorophthalic acid (CSDP acid) for X-ray crystallography and 2-methoxy-2-(1-naphthyl)propionic acid (M alpha NP acid) for H-1 NMR spectroscopy. In this review, the principles and applications of these X-ray and NMR methods are explained using mostly our own data.
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