Advances in the Construction Methods of Cyclopropane Skeleton and Their Applications

doi:10.6023/cjoc202507041

Abstract

The cyclopropane skeleton holds significant theoretical and practical value in diverse fields, such as medicinal chemistry and fuel chemistry, owing to its highly strained ring structure and favorable lipophilicity. This review systematically summarizes the strategies developed over the past two decades for constructing the cyclopropane framework, including cycloaddition reactions of carbenes and carbenoids with alkenes, ylide-mediated cyclizations, metallocyclopropane-involved cyclopropanations, intramolecular cyclopropanations, as well as emerging photocatalytic, electrocatalytic, and enzymatic cyclopropanation methods. Emphasis is placed on the mechanistic pathways, substrate compatibility, and stereoselectivity of the products. Furthermore, this review highlights the recent advances in the application of cyclopropane construction strategies across various domains, such as drug development (e.g., synthesis of antiviral and neuroregulatory agents), total synthesis of natural products, and the design of high-energy-density fuel molecules. Finally, the future development prospects of cyclopropane synthesis are discussed, pointing to the importance of novel high-efficiency catalysts (e.g., nano-supported and porous framework catalysts), advanced photocatalytic technologies, and greener synthetic methodologies as key research directions.

Key words: cyclopropane, carbine, cyclopropanation reaction, synthetic strategies, medicines, natural products, high-energy fuel

Cite this article

Junfeng Guo, Chunying Li, Ronggui Hu, Haojie Rong, Jiangwei Li, Yongmei Du, Yue Qin, Jian Lü, Dao'an Sun. Advances in the Construction Methods of Cyclopropane Skeleton and Their Applications[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 379-398.

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Fig. & Tab. 45

Scheme 1. Influence of cyclopropane on pharmacological efficacy as well as fuel density and volumetric calorific value

Scheme 2. Construction strategy of cyclopropanation

年份	作者	内容
2018	唐功利	总结了天然产物中环丙烷官能团的化学合成与生物合成策略, 主要包括卡宾参与的环丙烷化、分子内S_N2反应、环异构化以及生物合成等策略.
2018	Yury V. Tomilov	主要聚焦于供体-受体环丙烷(Donor-acceptor cyclopropanes, DACs)的合成方法, 包括亲核烯烃与重氮化合物和碘叶立德的反应, 以及亲电烯烃与硫叶立德的反应(Corey-Chaykovsky反应).
2021	Yury V. Tomilov	系统综述了重氮甲烷(CH₂N₂)催化环丙烷化的最新进展, 包括核心催化剂钯基催化剂(如Pd(OAc)₂), 以及安全合成技术和原位生成法, 解决CH₂N₂爆炸性难题; 底物适用性: 单/双取代烯烃、多烯、杂环烯烃均可环丙烷化, 但三取代烯烃需过量CH₂N₂(产率≤50%); 局限性: 不对称环丙烷化效果差(ee<2%).
2019	Marcos G. Suero	总结了2017~2019年光氧化还原催化自由基类卡宾环丙烷化的突破性进展.
2021	王也铭, 王自坤	总结了碘叶立德在有机合成中的研究进展, 其中涉及的环丙烷化反应主要包括金属催化、无金属催化(如PhI(OAc)₂/Bu₄NI体系)、光催化及无催化剂策略.

Table 1. A review of advances in cyclopropane construction methods

Scheme 3. Asymmetric cyclopropanation of olefins with ethyl diazoacetate catalyzed by chiral copper catalysts

Scheme 4. Mechanism of cyclopropanation with diazomethane catalyzed by different catalysts

序号	底物	产物	相对反应速率
序号	底物	产物	Pd(OAc)₂	Pd(acac)₂	(Ph₃P)₂PdCl₂
1			1	1	1
2			1.05	1.33	1.12
3			2.25	3.00	3.80
4			2.50	1.68	1.86
5			0.08^a	0.10	—
6			0.02	0.08	0.03
7			≈0.001	≈0.001	<0.002
8			0.18	0.24	0.24

Table 2. Relative reaction rates of a series of olefins catalyzed by Pd(OAc)2, Pd(acac)2, and (Ph3P)2PdCl2

Scheme 5. Schematic diagram of tube-in-tube reactor[1]

Scheme 6. Cyclopropanation of cyclohexene using chloroform as a dichlorocarbene precursor

Scheme 7. Dichlorocyclopropanation of terpenes

Scheme 8. Reductive dehalogenation of gem-dihalocyclopro- panes

Scheme 9. Literature-reported strategies for the dehalogenation of gem-dihalocyclopropanes

Scheme 10. Mechanism of the Simmons-Smith reaction

Scheme 11. Corey-Chaykovsky cyclopropanation reaction

Scheme 12. Mechanism of sulfur ylide addition to unsaturated hydrocarbons

Scheme 13. Synthesis of trans-(dioxo)-azabicyclo[3.1.0]-hexa- ne-carboxylate

Scheme 14. Three-component reaction of sulfonium salts with aldehydes and malononitrile in ethanol and ionic liquids

Scheme 15. Construction of cyclopropanes via reaction of sulfur ylides with methyl penta-2,4-dienoate

Scheme 16. Synthesis of 1,1-cyclopropanediesters using iodonium ylides[43]

Scheme 17. Catalyst-free cyclopropanation of electron-deficient alkenes using iodonium ylides

Scheme 18. Photocatalyzed cyclopropanation of alkenes with iodonium ylides under LED blue light irradiation

Scheme 19. Cyclopropane construction using alternative ylides

Scheme 20. Kulinkovich reaction involving aliphatic carboxylate esters

Scheme 21. Proposed mechanism of the Kulinkovich reaction

Scheme 22. Kulinkovich reaction involving N,N-dialkylamides

Scheme 23. Reactive intermediates in cyclopropane synthesis and a novel radical approach leveraging visible-light photoredox catalysis[13]

Scheme 24. Cyclopropanation of styrene with ethyl diazoacetate catalyzed by [Cr(Ph2phen)3](BF4)3

Scheme 25. Cyclopropanation of styrene using diethyl 2,2-dibromomalonate as a C1 synthon

Scheme 26. Electrocatalyzed cyclopropanation

Scheme 27. Iron porphyrin-catalyzed cyclopropanation of alkenes and P450 enzyme-catalyzed cyclopropanation

Scheme 28. Metal-reductive cyclopropanation

Scheme 29. Construction of cyclopropanes via Wolff-Kishner reduction methodology

Scheme 30. Ring contraction approaches to cyclopropane synthesis

Scheme 31. A general protocol for cyclopropane construction from alkyl malonates and activated alkenes

Scheme 32. Conversion of indole acryl alcohols to chiral cyclopropane intermediates

Scheme 33. Transformation of terminal alkenes utilizing the Simmons-Smith cyclopropanation protocol

Scheme 34. Ru-catalyzed asymmetric cyclopropanation of vinylindole 7 with ethyl diazoacetate

Scheme 35. Synthesis of pyridylcyclopropylamine 12 utilizing the Kulinkovich reaction

Scheme 36. Synthesis route of tecovirimat

Scheme 37. Total synthesis of the sesquiterpenoid natural product ishwarane

Scheme 38. Total synthesis of the sesquiterpene (＋)-omphadiol

Scheme 39. Total synthesis of pallambins A and B

Scheme 40. Synthesis of ivyane

Scheme 41. Cyclopropanation of myrcene

Scheme 42. Cyclopropanation of pinene

Scheme 43. Cyclopropanation of dimethylcyclopentadiene, 5-ethylene-2-norbornene, and tricyclopentadiene

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环丙烷骨架的构建及其应用研究进展