含氮芳香性杂环化合物的不对称氢化反应研究进展

doi:10.6023/cjoc202312004

摘要/Abstract

手性饱和含氮杂环结构广泛存在于天然产物、生物活性分子和药物分子中. 利用含氮芳杂环化合物的不对称氢化反应来构筑该类化合物是最为直接有效的方法之一. 然而, 由于含氮芳杂环化合物具有很强的共轭稳定性, 且产物中氮原子对金属催化剂具有毒化作用, 该类化合物的不对称氢化反应的发展要滞后很多, 研究报道也相对较少. 其中, 如何开发高效的催化体系来实现活化惰性底物的同时, 对反应的立体选择性进行精确调控是相关研究的关键问题. 目前, 一系列过渡金属以及有机小分子催化剂的开发已经引领该领域取得了一定进展. 鉴于不同类型催化剂的结构和性质对于催化活性、反应选择性及底物适用范围的显著影响, 根据催化剂的反应性进行分类, 系统综述了含氮芳香性杂环化合物不对称氢化反应的研究进展.

关键词: 氢化反应, 不对称催化, 手性含氮杂环

The structure of chiral saturated N-heterocyclic compounds widely exists in natural products, bioactive molecules, and drug molecules. Catalytic asymmetric hydrogenation of aromatic N-heterocycles is one of the most effective methods for the construction of these compounds. However, due to the strong conjugation stability of nitrogen-containing aromatic heterocyclic compounds and the poison effect of nitrogen atoms in the products on metal catalysts, the development of asymmetric hydrogenation reactions of these compounds lags far behind, and there are relatively few research reports. Therefore, how to develop efficient catalytic systems to activate the inert substrate and precisely control the stereoselectivity of the reaction is the key scientific issue of relevant research. In recent years, the development of a series of metal and organo catalysts has led to significant progress and shown broad prospects for its applications. Considering that the structures and properties of different catalysts have remarkable influence on the reactivity, selectivity, and substrate generality of the target transformations, an overview of asymmetric hydrogenation of aromatic N-heterocyclic compounds categorized is provided according to the types of catalysts.

Key words: hydrogenation reaction, asymmetric catalysis, chiral N-heterocyclic compound

引用此文

刘晨光. 含氮芳香性杂环化合物的不对称氢化反应研究进展[J]. 有机化学, 2024, 44(5): 1403-1422.

Chenguang Liu. Progress in Asymmetric Hydrogenation of Aromatic N-Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1403-1422.

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图/表 35

图1. 含有手性含氮杂环骨架的功能分子

Figure 1. Functional molecules containing chiral N-heterocyclic frameworks

图式1. 含氮芳杂环化合物不对称氢化构建手性含氮杂环骨架

Scheme 1. Construction of chiral N-heterocyclic frameworks via asymmetric hydrogenation of N-heteroaromatic compounds

图2. 含氮芳杂环化合物不对称氢化反应代表性催化体系

Figure 2. Representative catalytic systems for asymmetric hydrogenation (AH) of N-heteroaromatic compounds

图式2. 季铵化策略活化芳香含氮杂环化合物

Scheme 2. Quaternization strategy for activation of N-hetero- aromatic compounds

图式3. 配位辅助策略活化芳香含氮杂环化合物

Scheme 3. Substrate-directed strategy for activation of N-hetero- aromatic compounds

图式4. 去芳香性策略

Scheme 4. Dearomatization strategy

图式5. 铱催化剂前体的活化

Scheme 5. Activation of iridium catalyst precursor

图式6. 内球机制介导的含氮芳杂环不对称氢化反应

Scheme 6. Asymmetric hydrogenation of N-heteroaromatic compounds via inner-sphere mechanism

图式7. 铱催化喹啉的不对称氢化反应

Scheme 7. Iridium-catalyzed AH of quinolines

图式8. 铱催化喹啉不对称氢化反应中的配体效应

Scheme 8. Ligand effect in iridium-catalyzed AH of quinolines

图式9. 铱催化吲哚的不对称氢化反应

Scheme 9. Iridium catalyzed AH of indoles

图式10. 铱催化异喹啉的不对称氢化反应

Scheme 10. Iridium catalyzed AH of isoquinolines

图式11. 1,3-二取代异喹啉的不对称氢化反应及其在天然产物全合成中的应用

Scheme 11. AH of 1,3-disubstituted isoquinolines and its application in total synthesis of natural products

图式12. 铱催化活化吡啶的不对称氢化反应

Scheme 12. Iridium catalyzed AH of activated pyridines

图式13. 四齿配体配位的三价铱配合物的活化

Scheme 13. Activation of Ir(III) complex with tetradentate ligands

图式14. 铱催化喹喔啉的不对称氢化反应

Scheme 14. Iridium catalyzed AH of quinoxalines

图式15. 铱催化N-苄基-吡咯[1,2-a]吡嗪鎓盐的不对称氢化反应

Scheme 15. Iridium catalyzed AH of pyrrolo[1,2?a]pyrazinium salts

图式16. 铱催化喹唑啉盐酸盐的不对称氢化反应

Scheme 16. Iridium catalyzed AH of quinazolinium salts

图式17. 铱催化嘧啶的不对称氢化反应

Scheme 17. Iridium catalyzed AH of pyrimidines

图式18. 手性二胺/钌催化含氮芳杂环的不对称氢化反应

Scheme 18. Diamine/ruthenium complex catalyzed AH of N- heteroaromatic compounds

图式19. 钌催化N取代吡咯的不对称氢化反应

Scheme 19. Ruthenium catalyzed AH of N-substituted pyrroles

图式20. 钌催化N取代咪唑和噁唑的不对称氢化反应

Scheme 20. Ruthenium catalyzed AH of N-substituted imi- dazoles and oxazoles

图式21. NHC/钌催化喹喔啉化学选择性不对称氢化

Scheme 21. NHC-Ru-catalyzed chemoselective AH of quinoxalines

图式22. NHC/钌催化含多氮杂环化合物的不对称氢化反应

Scheme 22. NHC-Ru-catalyzed AH of multi N-heteroaromatic compounds

图式23. 铑催化N取代吲哚的不对称氢化反应

Scheme 23. Rhodium-catalyzed AH of N-substituted indoles

图式24. 铑催化3-取代吡啶盐的不对称氢化反应

Scheme 24. Rhodium-catalyzed AH of 3-substituted pyridinium salts

图式25. Zhaophos/铑配合物催化的含氮芳杂环的不对称氢化反应

Scheme 25. Zhaophos/Rh complex-catalyzed AH of N-hetero- aromatic compounds

图式26. 铑催化的吡唑[1,5-a]嘧啶的不对称氢化反应

Scheme 26. Rh-catalyzed AH of pyrazolo[1,5-a]pyrimidines

图式27. 质子酸活化钯催化剂的机制

Scheme 27. Activation of Palladium catalysts by proton acid

图式28. 钯催化含氮芳杂环化合物的不对称氢化反应

Scheme 28. Palladium-catalyzed AH of N-heteroaromatic compounds

图式29. 铁催化喹喔啉和苯并噁嗪的不对称氢化反应

Scheme 29. Iron-catalyzed AH of quinoxaline and benzoxazines

图式30. 锰催化喹啉和喹喔啉的不对称氢化反应

Scheme 30. Manganese-catalyzed AH of quinolines and quinoxalines

图式31. FLP催化含氮芳杂环的不对称氢化反应

Scheme 31. FLP-catalyzed AH of N-heteroaromatic compounds

图式32. 仿生接力催化体系介导的不对称还原反应

Scheme 32. Asymmetric reduction reactions mediated by bio- mimetic relay catalysis

图式33. 仿生接力催化体系在含氮芳杂环不对称氢化反应中的应用

Scheme 33. Biomimetic relay catalysis in AH of N-hetero- aromatic compounds

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