Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation★

doi:10.6023/A23040140

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (6): 646-656.DOI: 10.6023/A23040140 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Review

镍催化不对称氢化构建手性C—X键的研究进展^★

蔡新红, 陈建中^*(), 张万斌^*()

上海交通大学化学化工学院变革性分子前沿科学中心上海市手性药物分子工程重点实验室上海 200240

投稿日期:2023-04-17 发布日期:2023-05-15

作者简介:

蔡新红, 上海交通大学在读博士(导师: 张万斌教授), 主要研究方向为丰产金属催化的不对称氢化反应.

陈建中, 上海交通大学化学化工学院副研究员. 本科毕业于浙江工业大学; 硕士毕业于华东理工大学(导师: 赵敏副教授); 2013年博士毕业于上海交通大学(导师: 张万斌教授), 同年在本校从事博士后研究(导师: 颜德岳院士). 主要从事不对称催化研究, 药物和香料等合成工艺研究等.

张万斌, 上海交通大学化学化工学院讲席教授; 1997年在日本大阪大学取得博士学位; 1997年至2001年在日本大阪大学工学部应用化学系任助理教授; 2001年至2003年在日本三菱化学株式会社横滨综合研究所任主任研究员; 2003年至今任上海交通大学教授/特聘教授/讲席教授; 2017年起担任上海市手性药物分子工程重点实验室主任. 主要研究兴趣包括有机金属化学、不对称催化和制药过程化学.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(21991112); 国家自然科学基金(21702134); 国家自然科学基金(21772119)

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★

Xinhong Cai, Jianzhong Chen(), Wanbin Zhang()

Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Received:2023-04-17 Published:2023-05-15
Contact: *E-mail: 0091109001@sjtu.edu.cn; wanbin@sjtu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(21991112); National Natural Science Foundation of China(21702134); National Natural Science Foundation of China(21772119)

Chiral C—X (X=N, O, P, B, F, etc.) bond fragments are present in a wide variety of natural and pharmaceutically active molecules. Transition metal-catalyzed asymmetric hydrogenation is one of the most attractive strategies for the synthesis of these chiral compounds. Among the many transition metal catalysts, earth-abundant transition metals (iron, cobalt, nickel, and copper) have been used in asymmetric hydrogenation to replace rare metals (rhodium, ruthenium, iridium and palladium) due to their abundant reserves, low toxicity, and environmental friendliness. At present, this method for the construction of chiral C—X bonds has become a prominent trend in modern organic chemistry. Among them, the development of nickel catalysts has been relatively rapid. Based on this, the article will review the latest research in the preparation of compounds with chiral C—X bonds via nickel-catalyzed asymmetric hydrogenation using hydrogen. It is divided into five sections consisting of the construction of chiral C—N, C—O, C—P, C—B and C—F bonds by nickel-catalyzed asymmetric hydrogenation.

Key words: asymmetric hydrogenation, chiral C—X bonds, nickel catalysis, earth-abundant transition metals, active molecules

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Xinhong Cai, Jianzhong Chen, Wanbin Zhang. Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★[J]. Acta Chimica Sinica, 2023, 81(6): 646-656.

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Fig. & Tab. 28

Figure 1. Early studies on transition metal-catalyzed asymmetric hydrogenation

Figure 2. Representative compounds containing chiral C—N bonds

Figure 3. Nickel-catalyzed asymmetric hydrogenation of N-sulfonyl imines and its computed catalytic cycle

Figure 4. Product derivatizations of nickel-catalyzed asymmetric hydrogenation of N-sulfonyl imines

Figure 5. Nickel-catalyzed asymmetric hydrogenation of N-sulfonyl imines and product derivatizations, nickel-catalyzed asymmetric hydrogenation of α,β-unsaturated ketoimines

Figure 6. Nickel-catalyzed asymmetric hydrogenation of cyclic N-sulfonyl ketimino esters and product derivatizations

Figure 7. Nickel-catalyzed asymmetric hydrogenation of N-aryl imino esters and practical applications

Figure 8. Nickel-catalyzed asymmetric hydrogenation of hydrazones and practical applications

Figure 9. Nickel-catalyzed asymmetric hydrogenation of cyclic N-sulfonylimines and product derivatizations

Figure 10. Nickel-catalyzed asymmetric hydrogenation of oximes, its computed catalytic cycle and product derivatizations

Figure 11. Nickel-catalyzed asymmetric hydrogenation of enamides

Figure 12. Computed catalytic cycle of nickel-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins

Figure 13. Nickel-catalyzed asymmetric hydrogenation of 2-amidoacrylates, product derivatizations and practical applications

Figure 14. Proposed mechanism of nickel-catalyzed asymmetric hydrogenation of 2-amidoacrylates

Figure 15. Nickel-catalyzed asymmetric hydrogenation of 2-oxazolones/ enamines and product derivatizations

Figure 16. Representative compounds containing chiral C—O bonds

Figure 17. Nickel-catalyzed asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides and α-amino ketone hydrochlorides

Figure 18. Nickel-catalyzed asymmetric hydrogenation of α-keto-β-lactams and product derivatizations

Figure 19. Nickel-catalyzed asymmetric hydrogenation of aliphatic ketoacids, its proposed mechanism and product derivatizations

Figure 20. Nickel-catalyzed asymmetric hydrogenation of aromatic ketoacids and product derivatizations

Figure 21. Nickel-catalyzed asymmetric hydrogenation of γ-keto acids, esters, amides and product derivatizations

Figure 22. Representative compounds containing chiral C—P bonds

Figure 23. Nickel-catalyzed asymmetric hydrogenation of α-substituted vinylphosphine compounds and its proposed mechanism

Figure 24. Product derivatizations of nickel-catalyzed asymmetric hydrogenation of α-substituted vinylphosphine compounds

Figure 25. Nickel-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated phosphine oxides/phosphonates/phosphoric acids

Figure 26. Nickel-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters and product derivatizations

Figure 27. Representative compounds containing chiral C—F bonds

Figure 28. Nickel-catalyzed asymmetric hydrogenation of tetra substituted fluorinated enamides

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镍催化不对称氢化构建手性C—X键的研究进展^★

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★

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镍催化不对称氢化构建手性C—X键的研究进展★

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation★

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Abstract

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Fig. & Tab. 28

References 43

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镍催化不对称氢化构建手性C—X键的研究进展^★

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★