Research Progress in Asymmetric Hydrogenation of Small-Ring Compounds

doi:10.6023/cjoc202603025

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3495-3505.DOI: 10.6023/cjoc202603025 Previous Articles Next Articles

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小环化合物的不对称氢化研究进展

杨爽^a, 房新强^a^,^b^,^*()

^a 中国科学院福建物质结构研究所结构化学全国重点实验室福州 350100
^b 安徽师范大学化学与材料科学学院功能分子固体教育部重点实验室安徽芜湖 241002

收稿日期:2026-03-18 修回日期:2026-04-20 发布日期:2026-06-17
通讯作者: 房新强
基金资助:
国家自然科学基金(22571300); 国家自然科学基金(22071242); 中国科学院海西研究院自主部署项目研究计划(CXZX-2022-GH03); 结构化学国家重点实验室配套支持计划(E555YA4001)

Research Progress in Asymmetric Hydrogenation of Small-Ring Compounds

Shuang Yang^a, Xinqiang Fang^a^,^b^,^*()

^a State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350100
^b Key Laboratory of Functional Molecular Solids, Ministry of Education, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002

Received:2026-03-18 Revised:2026-04-20 Published:2026-06-17
Contact: Xinqiang Fang
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
Supported by:
National Natural Science Foundation of China(22571300); National Natural Science Foundation of China(22071242); Self-deployment Project Research Program of Haixi Institutes, Chinese Academy of Sciences(CXZX-2022-GH03); supporting program of State Key Laboratory of Structural Chemistry(E555YA4001)

Given that chiral three- and four-membered cyclic compounds are widely present as key structural units in bioactive molecules and are frequently employed as crucial intermediates in fields such as pharmaceutical development, their synthetic research holds a significant position in the realm of organic chemistry. Transition metal-catalyzed asymmetric hydrogenation reactions (including pressurized hydrogenation and transfer hydrogenation) are ideal methods for constructing chiral small-ring compounds owing to their remarkable catalytic efficiency, excellent enantioselectivity, and scalability. However, various challenges exist and slow down the related development. This review systematically summarizes the latest research progress in the field of asymmetric hydrogenation of small-ring compounds, with a particular focus on studies related to four- membered ring substrates (such as β-lactams, cyclobutanones, cyclobutenones, and cyclobutenediones) and three-membered ring substrates (including gem-difluorocyclopropenyl esters and gem-difluorocyclopropenyl ketones).

Key words: asymmetric hydrogenation, three-membered rings, four-membered rings, enantioselectivity

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Shuang Yang, Xinqiang Fang. Research Progress in Asymmetric Hydrogenation of Small-Ring Compounds[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3495-3505.

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Fig. & Tab. 15

Scheme 1. Asymmetric hydrogenation of α-alkylidene β-lactams

Scheme 2. Asymmetric hydrogenation of α-alkylidene cyclobutanones

Scheme 3. Asymmetric hydrogenation of α-alkylidene benzo-fused cyclobutanones

Scheme 4. Asymmetric hydrogenation of α-keto-β-lactams

Scheme 5. Ru-catalyzed ATH for cyclobutenone formation

Scheme 6. Ru-catalyzed ATH for cyclobutanediol formation

Scheme 7. Ru-catalyzed ATH for cyclobutenediol formation

Scheme 8. Classical kinetic resolution of cyclobutenone

Scheme 9. Parallel kinetic resolution of cyclobutenone

Scheme 10. Dynamic kinetic resolution of cyclobutenone

Scheme 11. Asymmetric hydrogenation of gem-dichlorocyclobutenones

Scheme 12. Asymmetric hydrogenation of hemisquaramides

Scheme 13. Asymmetric hydrogenation of gem-difluorocyclopropenyl esters

Scheme 14. Asymmetric hydrogenation of gem-difluorocyclopropenyl ketones

Scheme 15. Asymmetric hydrogenation of gem-difluorocyclopropenyl esters or ketones

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小环化合物的不对称氢化研究进展

Research Progress in Asymmetric Hydrogenation of Small-Ring Compounds

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