Citation: Dong Ziyang, Yang Zhanhui, Xu Jiaxi. Structural Modifications and Chiral Applications of Brucine[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4101-4121. doi: 10.6023/cjoc202004049 shu

Structural Modifications and Chiral Applications of Brucine

Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029

Corresponding author: Yang Zhanhui, zhyang@mail.buct.edu.cn
Received Date: 29 April 2020
Revised Date: 17 June 2020
Available Online: 8 July 2020
Fund Project: Project supported by the Beijing Natural Science Foundation (No. 2202041) and the National Natural Science Foundation of China (No. 21602010)the Beijing Natural Science Foundation 2202041the National Natural Science Foundation of China 21602010

Figures(67)

The recent advances on the structural modifications and chiral applications of Brucine are reviewed. Brucine is a naturally occuring molecule with multiple functional groups and a complex stereochemical structure. Selective structural modification of brucine is challenging, and a variety of methods to achieve selective modifications at its specific site are available. The aryl moiety undergoes demethoxypentafluorophenylation, and the amide moiety undergoes the condensation with primary amine, deoxycyanation, deoxygenative reduction, and α-oximation. The tertiary amine moiety undergoes N-oxidation, formal carbene insertions of C-N or α-C-H bonds, three-component reactions with benzynes and phenols, N-amidation with nitrene, and N-alkylation with halogenated hydrocarbons. The C=C subunit undergoes dihydroxylation and hydrogenation, while the ether subunit undergoes hydrogenative cleavage. The modified structures have high potential medicinal values. As a chiral resolution reagent, brucine has been widely used in the resolution of racemic carboxylic acids, phosphoric or phosphonic acids, phenols, alcohols and some drugs. Additionally, brucine and its modified structures also find applications as chiral auxiliaries, chiral catalysts or chiral ligands in asymmetric synthesis and catalysis.
- brucine,
- structural modification,
- chiral resolution,
- asymmetric synthesis
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沈阳化工大学材料科学与工程学院沈阳 110142