Methods and Application of Absolute Configuration Assignment for Chiral Compounds

doi:10.6023/cjoc202108047

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 424-433.DOI: 10.6023/cjoc202108047 Previous Articles Next Articles

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手性化合物绝对构型确定的方法与应用

葛锐^a, 朱园园^b, 王海峰^a^,^c^,^*(), 古双喜^a^,^c^,^*()

a 武汉工程大学化工与制药学院绿色化工过程教育部重点实验室武汉 430205
b 武汉工程大学化学与环境工程学院武汉 430205
c 武汉工程大学新型反应器与绿色化学工艺湖北省重点实验室武汉 430205

收稿日期:2021-08-24 修回日期:2021-09-18 发布日期:2022-02-24
通讯作者: 王海峰, 古双喜
基金资助:
国家自然科学基金(21877087); 国家自然科学基金(22074114); 国家自然科学基金(20602164); 湖北省自然科学基金(2020CFB623); 绿色化工过程教育部重点实验室开放基金(GCP20200201); 新型反应器与绿色化学工艺湖北省重点实验室(武汉工程大学)开放基金(40201002)

Methods and Application of Absolute Configuration Assignment for Chiral Compounds

Rui Ge^a, Yuanyuan Zhu^b, Haifeng Wang^a^,^c(), Shuangxi Gu^a^,^c()

a Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan 430205
b School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205
c Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan 430205

Received:2021-08-24 Revised:2021-09-18 Published:2022-02-24
Contact: Haifeng Wang, Shuangxi Gu
Supported by:
National Natural Science Foundation of China(21877087); National Natural Science Foundation of China(22074114); National Natural Science Foundation of China(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)

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.

Key words: chiral chemistry, chiral compounds, absolute configuration assignment, nuclear magnetic resonance (NMR), X-ray diffraction (XRD), spectroscopy

Cite this article

Rui Ge, Yuanyuan Zhu, Haifeng Wang, Shuangxi Gu. Methods and Application of Absolute Configuration Assignment for Chiral Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 424-433.

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Fig. & Tab. 12

Figure 1. An overview of absolute configuration determination methods

Figure 2. Diagram of modified Mosher ester configuration pattern

Figure 3. ΔδRS values for bis-MPA esters of compounds 1~3

Figure 4. Chemical structures of various aryl methoxy acetic acids

Figure 5. Chemical structures of MBNC and MNCB

Figure 6. Chemical structures of THENA, THENA-d2 and F-THENA reagents

Figure 8. (a) Structure of two enantiomers of β-fucofuranoside and α-arabinofuranoside; (b) Δδ values of tertiary alcohols 4~6

Figure 9. Schematic diagram of XRD

Figure 10. Crystal structure of compound 7

Figure 11. Schematic diagram of ECD

Figure 12. Chemical structures of compounds 8~10

Figure 13. Absolute configuration of secondary alcohols by the HBTM catalyst

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手性化合物绝对构型确定的方法与应用

Methods and Application of Absolute Configuration Assignment for Chiral Compounds

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