电化学合成氨基酸类化合物的研究进展

doi:10.6023/cjoc202102043

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3034-3049.DOI: 10.6023/cjoc202102043 上一篇下一篇

所属专题：有机电合成虚拟专辑

综述与进展

电化学合成氨基酸类化合物的研究进展

王娜娜^a, 徐敬成^a, 梅海波^a, Hiroki Moriwaki^b, Kunisuke Izawa^b, Vadim A. Soloshonok^c^,^d^,^*(), 韩建林^a^,^*()

a 南京林业大学化学工程学院江苏省林业资源高效加工利用协调创新中心林产化学与材料国际创新高地南京 210037 中国
b 浜理药品株式会社大阪 533-0024 日本
c 巴斯克大学有机化学学院圣塞巴斯蒂安 20018 西班牙
d 巴斯克IKERBASQUE科学基金会毕尔巴鄂 48011 西班牙

收稿日期:2021-02-23 修回日期:2021-04-07 发布日期:2021-04-25
通讯作者: Vadim A. Soloshonok, 韩建林
基金资助:
国家自然科学基金(21761132021)

Electrochemical Approaches for Preparation of Tailor-Made Amino Acids

Nana Wang^a, Jingcheng Xu^a, Haibo Mei^a, Hiroki Moriwaki^b, Kunisuke Izawa^b, Vadim A. Soloshonok^c^,^d(), Jianlin Han^a()

a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
b Hamari Chemical Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan
c Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain
d IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain

Received:2021-02-23 Revised:2021-04-07 Published:2021-04-25
Contact: Vadim A. Soloshonok, Jianlin Han
Supported by:
National Natural Science Foundation of China(21761132021)

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摘要/Abstract

氨基酸类化合物在现代医药化学研究和药物设计开发方面具有非常重要的作用, 一直以来, 开发高效的合成方法学来制备这些氨基酸类化合物的研究吸引了化学家们广泛的研究兴趣. 另一方面, 近些年电化学反应逐渐兴起成为一种绿色可再生的合成手段, 是有机合成化学领域的研究热点, 其在氨基酸的合成方面的应用也受到了极大的关注. 本综述第一次较为系统全面地总结了近些年有关电化学手段合成氨基酸的研究进展, 讨论了这些电化学方法在合成氨基酸类化合物方面的实际应用的可行性、具备的优势以及存在的一些局限, 为氨基酸绿色合成方面的研究提供了一定的参考.

关键词: 电化学反应, 氨基酸, 自由基反应, 不对称合成, 镍配合物

Due to the pivotal role of tailor-made amino acids in modern medicinal chemistry research and drug design, the interest in the development of synthetic methodology for preparation of these compounds is at an all-time high. Currently, electrochemical approaches for synthesis of amino acids are being actively pursued to take the advantage of sustainability and green chemistry facets offered by the electrochemistry. This work presents the first specially focused, comprehensive treatment of the literature data related to synthesis of amino acids via electrochemical means. Aspects of practicality, benefits and current shortcoming of this approach are critically discussed.

Key words: electrochemical reactions, amino acids, radical reactions, asymmetric synthesis, Ni-complex

引用此文

王娜娜, 徐敬成, 梅海波, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, 韩建林. 电化学合成氨基酸类化合物的研究进展[J]. 有机化学, 2021, 41(8): 3034-3049.

Nana Wang, Jingcheng Xu, Haibo Mei, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, Jianlin Han. Electrochemical Approaches for Preparation of Tailor-Made Amino Acids[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3034-3049.

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图/表 28

Scheme 1. General asymmetric synthesis of α-AAs using Ni(II)- complexes methodology

Scheme 2. Electrochemical Michael addition of Ni-complex

Scheme 3. Possible mechanism for the electrochemical Michael addition of Ni-complex

Scheme 4. Self-coupling of Gly-Ni 4 and Ala-Ni 7

Scheme 5. Cathodic reductive dimerization Ni-complex 11

Scheme 6. Electrochemical reaction of Ni-complex 1 with C60

Scheme 7. Electrochemical thioalkylation of Ni-complex 4

Scheme 8. Electrochemical hydroxyalkylation of the Ni(II)- complex

Scheme 9. Possible mechanism for the electrochemical hydroxyalkylation of the Ni(II)-complex

Scheme 10. Electrochemical bromination and sulfanylation reaction

Scheme 11. Proposed mechanism for electrochemical bromination and sulfanylation reaction

Scheme 12. Synthesis of alanine 32

Scheme 13. Synthesis of amino acids 35

Scheme 14. α-Keto acids as substrates of H2/α-keto acid EFC for preparation of chiral amino acids

Scheme 15. Electrochemical amination for the synthesis of AAs

Scheme 16. Electrochemical synthesis of amino acids from molybdenum complex

Scheme 17. Electrochemical reaction of the fluorine-containing imine with carbon dioxide

Scheme 18. Possible mechanism for this electrochemical carboxylation reaction

Scheme 19. Electrochemical reaction of imine with carbon dioxide

Scheme 20. Proposed mechanism for the electrochemical reaction between imine and carbon dioxide

Scheme 21. Electrocarboxylation reactions of imine under continuous flow conditions

Scheme 22. Electrosynthesis of 6-aminonicotinic acid

Scheme 23. Synthesis of N-acyl-α-amino ester via anodic oxidation and cobalt-catalyzed carbonylation reaction

Scheme 24. Proposed mechanism for this two-step reaction

Scheme 25. Electrochemical decarboxylation of acylaminomalonic acid diethyl esters

Scheme 26. Synthesis of 2,5-diaminoadipic acid derivatives and 2,7-diaminosuberic acid derivatives by Kolbe electrolysis

Scheme 27. Synthesis of diaminodicarboxylic acid derivatives

Scheme 28. Electrochemical reduction of methyl 5-nitro-4-oxopentanate

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电化学合成氨基酸类化合物的研究进展

Electrochemical Approaches for Preparation of Tailor-Made Amino Acids

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