供体-受体氮杂环丙烷碳-碳键断裂的环加成反应研究进展

doi:10.6023/cjoc202303026

摘要/Abstract

氮杂环丙烷有两种不同的开环方式: 一种是碳-氮键断裂开环, 另一种是碳-碳键断裂开环. 其中, 氮杂环丙烷以碳-氮键断裂的反应已经有很多综述报道. 主要概述了近二十年来供体-受体(Donor-Acceptor, D-A)氮杂环丙烷以碳-碳键断裂的环加成反应研究进展. 在合适催化剂作用下, D-A氮杂环丙烷经碳-碳键断裂开环形成亚胺叶立德, 该叶立德可以和醛、亚胺、烯烃、炔烃和吲哚等发生[3+n]环加成反应.

关键词: D-A氮杂环丙烷, 碳-碳键断裂, 环加成反应, 亚胺叶立德

There are two different ring-opening modes of aziridines: ring-opening of aziridines via carbon-nitrogen bond cleavage, and ring-opening of aziridines via carbon-carbon bond cleavage. Among them, the reaction of aziridines via carbon-nitrogen bond cleavage has been reported in many reviews. The cycloaddition reactions of donor-acceptor (D-A) aziridines via carbon-carbon bond cleavage in recent 20 years are mainly summarized. Under some proper catalysts, the ring-opening of D-A aziridines via carbon-carbon bond cleavage yield azomethine ylides, which can undergo [3+n] cycloaddition reaction with aldehydes, imines, alkenes, alkynes, indoles etc.

Key words: D-A aziridines, carbon-carbon bond cleavage, cycloaddition reaction, azomethine ylide

引用此文

陈祖良, 魏颖静, 张俊良. 供体-受体氮杂环丙烷碳-碳键断裂的环加成反应研究进展[J]. 有机化学, 2023, 43(9): 3078-3088.

Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.

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图/表 24

图式1. 氮杂环丙烷两种不同断键方式

Scheme 1. Two different ring-opening modes of aziridines

图式2. 路易斯酸促进下D-A氮杂环丙烷碳-碳键断裂

Scheme 2. Lewis acid-promoted carbon-carbon bond cleavage of D-A aziridines

图式3. Y(OTf)3催化下D-A氮杂环丙烷和烯烃的[3+2]环加成反应

Scheme 3. Y(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkenes

图式4. D-A氮杂环丙烷和烯烃的[3+2]环加成反应的可能反应机理

Scheme 4. Plausible mechanism of [3+2] cycloaddition reaction of D-A aziridines with alkenes

图式5. 路易斯酸催化下D-A氮杂环丙烷和共轭二烯的分子内[3+2]环加成反应

Scheme 5. Lewis acid-catalyzed intramolecular [3+2] cycloaddition reaction of D-A aziridines with conjugated dienes

图式6. Sc(OTf)3催化下D-A氮杂环丙烷和手性烯烃的[3+2]环加成反应

Scheme 6. Sc(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with methylene exo-glycals

图式7. Sc(OTf)3催化下D-A氮杂环丙烷和炔烃的[3+2]环加成反应

Scheme 7. Sc(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkynes

图式8. Au/Yb(OTf)3催化下D-A氮杂环丙烷和炔醇/胺的[3+2]环加成反应

Scheme 8. Au/Yb(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkynyl alcohols/amines

图式9. 路易斯酸催化下D-A氮杂环丙烷和醛/亚胺的[3+2]环加成反应

Scheme 9. Lewis Acid-catalyzed [3+2] cycloaddition reaction of D-A aziridines with aldehydes/imines

图式10. Fe(OTf)3催化下D-A氮杂环丙烷和吲哚的[3+2]环加成反应

Scheme 10. Fe(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with indoles

图式11. HOTf催化下D-A氮杂环丙烷和腈类化合物的[3+2]环加成反应

Scheme 11. HOTf-catalyzed [3+2] cycloaddition reaction of D-A aziridines with nitriles

图式12. Y(OTf)3催化下D-A氮杂环丙烷和1,3,5-三嗪烷类类化合物的[3+2]环加成反应

Scheme 12. Y(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with 1,3,5-triazinanes

图式13. D-A氮杂环丙烷和烯酮亚胺类化合物的[3+2]环加成反应

Scheme 13. [3+2] cycloaddition reaction of D-A aziridines with ketenimines

图式14. MgI2催化下D-A氮杂环丙烷和1,4-二硫-2,5-二醇的[3+3]环加成反应

Scheme 14. MgI2-catalyzed [3+3] cycloaddition reaction of D-A aziridines with 1,4-dithiane-2,5-diol

图式15. Gd(OTf)3催化下D-A氮杂环丙烷和N,N-二烷基-3-烯基苯胺的[3+3]环加成反应

Scheme 15. Gd(OTf)3-catalyzed [3+3] cycloaddition reaction of D-A aziridines with N,N-dialkyl-3-vinylanilines

图式16. D-A氮杂环丙烷和β-(2-吲哚)-α,β-不饱和酮的[3+3]环加成反应

Scheme 16. [3+3] cycloaddition reaction of D-A aziridines with β-(indol-2-yl)-α,β-unsaturated ketones

图式17. Y(OTf)3催化下D-A氮杂环丙烷和异氰的[3+1+1]或[3+1]环加成反应

Scheme 17. Y(OTf)3-catalyzed [3+1+1] or [3+1] cycloaddition reaction of D-A aziridines with isocyanides

图式18. MgI2催化下D-A氮杂环丙烷和D-A环丙烷的环加成反应及其机理

Scheme 18. MgI2-catalyzed cycloaddition of D-A aziridines with D-A cyclopropanes and their mechanism

图式19. D-A氮杂环丙烷和醛的不对称[3+2]环加成反应

Scheme 19. Asymmetric [3+2] cycloaddition of D-A aziridines with aldehydes

图式20. D-A氮杂环丙烷和烯烃的不对称[3+2]环加成反应

Scheme 20. Asymmetric [3+2] cycloaddition of D-A aziridines with alkenes

图式21. D-A氮杂环丙烷和炔烃的不对称[3+2]环加成反应

Scheme 21. Asymmetric [3+2] cycloaddition of D-A aziridines with alkynes

图式22. D-A氮杂环丙烷和吲哚的不对称[3+2]环加成反应

Scheme 22. Asymmetric [3+2] cycloaddition of D-A aziridines with indoles

图式23. D-A氮杂环丙烷和烯烃的不对称[3+3]环加成反应

Scheme 23. Asymmetric [3+3] cycloaddition of D-A aziridines with aklkenes

图式24. D-A氮杂环丙烷和异氰的不对称[3+1]环加成反应

Scheme 24. Asymmetric [3+1] cycloaddition of D-A aziridines with isocyanides

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