Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 42, Issue 2, Pages 424-433Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202108047
Keywords
chiral chemistry; chiral compounds; absolute configuration assignment; nuclear magnetic resonance (NMR); X-ray diffraction (XRD); spectroscopy
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Funding
- National Natural Science Foundation of China [21877087, 22074114, 20602164]
- Natural Science Foundation of Hubei Province [2020CFB623]
- Key Laboratory for Green Chemical Process of Ministry of Education Open Fund [GCP20200201]
- Hubei Key Laboratory of Novel Reactor and Green Chemical Technology (Wuhan Institute of Technology) Open Fund [40201002]
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This article reviews the methods used to determine the absolute configuration of chiral compounds and provides an overview of their principles and applications.
The absolute configuration (AC) assignment of chiral molecules is crucial to the research and application of chiral chemistry. In recent years, various methods for the AC determination for chiral compound fall mainly into three categories according to their principles. The first is the nuclear magnetic resonance (NMR)-based method for determining the AC of chiral compound by exciting the nucleus of the chiral compound in the chiral environment, including the NMR-based method using aromatic ring diamagnetic shielding effect and the NMR method using sugar shift effect. The second is X-ray diffraction (XRD) methods based on atomic resonance scattering, including single crystal and powder XRD. The third is based on the enantiomer refraction and absorption of polarized light, including optical rotation spectroscopy, electronic circular dichroism, vibration circular dichroism and vibration Raman spectroscopy. In addition, other methods such as enzyme-based and homobenzotetramisole (HBTM)-based methods are supplementary. Based on our research experiences in chiral fluorescent recognition and chiral drugs, the principles and application of these methods, aiming to afford beneficial references for chiral chemists and related workers are reviewed.
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