氮杂环卡宾催化构筑含七元环结构的研究进展

doi:10.6023/cjoc202109020

摘要/Abstract

七元环作为重要的结构单元广泛存在于多种天然产物、活性化合物和药物分子中. 与五、六元环结构相比, 七元环的构筑更具挑战性, 且合成方法相对较少. 因此, 发展高效构筑七元环结构的方法具有重要意义. 氮杂环卡宾(NHC)为重要的有机催化剂, 其共价催化特性为高效构筑多种新颖手性结构提供了独特方法. 尽管该领域已取得重要进展, 然而, 目前大量研究仍集中于构筑五、六元环结构. 综述了近年来利用NHC催化策略构筑七元环结构的研究进展. 通过对NHC催化构筑七元环结构合成策略的总结, 旨在启发从事相关领域的合成化学家发展更多高效构筑七元环的新策略.

关键词: 氮杂环卡宾, 七元环, 不对称合成, 有机催化

The seven-membered rings represent an important structural motif and have found wide presence in natural products, biologically active molecules and drugs. In contrast to the five- and six-membered rings, the construction of seven- membered ring remains challenging. Thus, the developing efficient strategies for the synthesis of seven-membered rings is very desirable. N-Heterocyclic carbene (NHC) organocatalysis has been recognized as a powerful and unique tool for the quick construction of complex molecular architectures. Nevertheless, whereas significant advances have been made using NHC as catalysis. However, most of these works concentrated on the assembly of five or six-membered rings. This review highlights the developments and new advances for the construction of seven-membered rings catalyzed by NHC. The aim of this review is to provide an overview of this area and inspire synthetic chemists to develop more efficient and novel strategies for the construction of seven-membered rings.

Key words: N-heterocyclic carbenes, seven-membered ring, asymmetric synthesis, organocatalysis

引用此文

姚婷, 李佳燕, 王佳明, 赵常贵. 氮杂环卡宾催化构筑含七元环结构的研究进展[J]. 有机化学, 2022, 42(4): 925-944.

Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.

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图/表 42

图1. 含七元环结构的天然产物和药物举例

Figure 1. Selected examples of natural products and drugs containing seven-membered ring

图式1. NHC催化合成1,3-二氮杂?结构

Scheme 1. Synthesis of 1,3-diazepine structure catalyzed by NHC

图2. 1,3-二氮杂?的合成机理

Figure 2. Mechanism for the synthesis of 1,3-diazepine

图式2. NHC催化合成1,2-二氮杂?结构

Scheme 2. Synthesis of 1,2-diazepine structure catalyzed by NHC

图3. 1,2-二氮杂?的合成机理

Figure 3. Mechanism for the synthesis of 1,2-diazepine

图式3. NHC催化合成1,2-二氮杂?结构

Scheme 3. Synthesis of 1,2-diazepine structure catalyzed by NHC

图4. 1,2-二氮杂?的合成机理

Figure 4. Mechanism for the synthesis of 1,2-diazepine

图式4. NHC催化合成苯并氮杂?结构

Scheme 4. Synthesis of benzoazepine structure catalyzed by NHC

图式5. NHC催化合成吲哚螺环-苯并呋喃氮杂?

Scheme 5. Synthesis of spirocyclic oxindole-benzofurazinone catalyzed by NHC

图5. 螺-1,2-二氮杂?的合成机理

Figure 5. Mechanism for the synthesis of spiro-1,2-diazepine

图式6. NHC催化合成苯并呋喃氮杂?

Scheme 6. Synthesis of benzofurazepine catalyzed by NHC

图6. 苯并呋喃氮杂?的合成机理

Figure 6. Mechanism for the synthesis of benzofurazepine

图式7. NHC催化合成1,5-苯并二氮杂?结构

Scheme 7. Synthesis of 1,5-benzodiazepine structure catalyzed by NHC

图7. 1,5-苯并二氮杂?的合成机理

Figure 7. Mechanism for the synthesis of 1,5-benzodiazepine

图式8. NHC催化合成螺环内酰胺羟吲哚

Scheme 8. Synthesis of spiro-lactam hydroxyindole catalyzed by NHC

图8. 螺环内酰胺羟吲哚的合成机理

Figure 8. Mechanism for the synthesis of spiro-lactam hydroxyindole

图式9. NHC和苯亚磺酸盐共催化合成氮杂[1,2-α]-吲哚

Scheme 9. Synthesis of aza[1,2-α]-indole by cooperative NHC and benzenesulfinate

图9. 氮杂[1,2-α]-吲哚的合成机理

Figure 9. Mechanism for the synthesis of aza [1,2-α]-indole

图式10. NHC催化合成氮杂[1,2-α]-吲哚

Scheme 10. Synthesis of aza [1,2-α]-indole catalyzed by NHC

图10. 氮杂[1,2-α]-吲哚的合成机理

Figure 10. Mechanism for the synthesis of aza [1,2-α]-indole

图式11. NHC催化合成4-氮杂内酯

Scheme 11. Synthesis of 4-azalactone catalyzed by NHC

图11. 4-氮杂内酯的合成机理

Figure 11. Mechanism for the synthesis of 4-azalactone

图式12. NHC催化合成苯并二氧杂环己酮

Scheme 12. Synthesis of benzodioxepinone catalyzed by NHC

图12. 苯并二氧杂环己酮的合成机理

Figure 12. Mechanism for the synthesis of benzodioxepinone

图式13. NHC催化构筑苯并ε-内酯

Scheme 13. Synthesis of benzo-ε-lactone catalyzed by NHC

图13. 苯并ε-内酯的合成机理

Figure 13. Mechanism for the synthesis of benzo-ε-lactone

图式14. NHC催化合成ε-内酯结构

Scheme 14. Synthesis of ε-lactone structure catalyzed by NHC

图14. ε-内酯的合成机理

Figure 14. Mechanism for the synthesis of ε-lactone

图式15. NHC催化合成噻唑稠合的ε-内酯

Scheme 15. Synthesis of thiazole fused ε-lactone catalyzed by NHC

图15. 噻唑稠合的ε-内酯的合成机理

Figure 15. Mechanism for the synthesis of thiazole fused ε- lactone

图式16. NHC与路易斯酸Ti(OiPr)4共催化合成桥联己内酯

Scheme 16. Synthesis of bridged caprolactone through cooperative catalysis of NHC and lewis acid Ti(OiPr)4

图16. 桥联己内酯的合成机理

Figure 16. Mechanism for the synthesis of bridged caprolactone

图式17. NHC催化合成螺苯并氧杂酮

Scheme 17. Synthesis of spiro-benzoxanone catalyzed by NHC

图17. 螺苯并氧杂酮的合成机理

Figure 17. Mechanism for the synthesis of spiro-benzoxanone

图式18. NHC催化合成苯并[1,5]二硫杂环庚烷-2-酮

Scheme 18. Synthesis of benzo[1,5]dithiepin-2-one catalyzed by NHC

图18. 苯并[1,5]二硫杂环庚烷-2-酮的合成机理

Figure 18. Mechanism for the synthesis of benzo [1,5] dithiepin-2-one

图式19. NHC/钯协同催化合成苯并氮杂?结构

Scheme 19. Synthesis of benzazepine catalyzed by cooperative NHC/palladium

图19. 苯并氮杂?的合成机理

Figure 19. Mechanism for the synthesis of benzazepine

图式20. NHC/钯协同催化合成ε-己内酯

Scheme 20. Synthesis of ε-caprolactone catalyzed by cooperative NHC/Pd

图20. ε-己内酯的合成机理

Figure 20. Mechanism for the synthesis of ε-caprolactone

图式21. NHC和钯协同催化合成2,3-苯并二氮杂?结构

Scheme 21. Synthesis of 2,3-benzodiazepines structure catalyzed by cooperative NHC/Pd

图21. 2,3-苯并二氮杂?的合成机理

Figure 21. Mechanism for the synthesis of 2,3-benzodiazepines

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