Zirconium Lewis Acid-Catalyzed de Mayo-Type Ring Expansion of Cyclic β-Dicarbonyls

doi:10.6023/cjoc202607015

Chinese Journal of Organic Chemistry Previous Articles

ARTICLE

锆路易斯酸催化的环状β-二羰基化合物的de Mayo型扩环反应

王钧锋^a, 刘芮碹^a, 米学玲^a,*, 罗三中^b

^a北京师范大学,化学学院北京 100875;
^b清华大学,化学系,基础分子科学中心北京 100084

收稿日期:2026-07-15 修回日期:2026-07-31
基金资助:
国家自然科学基金(22393891)及国家重点研发计划(2023YFA1506401 and 2023YFA1506402)资助项目.

Zirconium Lewis Acid-Catalyzed de Mayo-Type Ring Expansion of Cyclic β-Dicarbonyls

Junfeng Wang^a, Ruixuan Liu^a, Xueling Mi^a,*, Sanzhong Luo^b

^aCollege of Chemistry, Beijing Normal University, Beijing, 100875;
^bCenter of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, 100084

Received:2026-07-15 Revised:2026-07-31
Contact: ^*E-mail: xlimi@bnu.edu.cn
Supported by:
Natural Science Foundation of China (22393891), the National Key R&D Program of China (2023YFA1506401 and 2023YFA1506402).

1. .pdf(4583KB)

Abstract

Zirconium-Lewis acid was developed to facilitate a de Mayo-type ring expansion reaction in the absence of external photosensitizers and additives. The reaction proceeds through a [2+2] cycloaddition and retro-Aldol sequence between cyclic β-ketocarbonyls and alkenes, which are compatible with various substrates in good yields. Through this strategy, a series of functionalized medium sized-ring skeletons can be constructed starting from readily available starting materials.

Key words: de Mayo reaction, Ring expansion, Zirconium Lewis acid-catalysis, β-ketocarbonyls

Cite this article

Junfeng Wang, Ruixuan Liu, Xueling Mi, Sanzhong Luo. Zirconium Lewis Acid-Catalyzed de Mayo-Type Ring Expansion of Cyclic β-Dicarbonyls[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202607015.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yan Luo, Zhangwei Liu, Zhaolei Hu, Hongyan Bi, Dongliang Mo. Recent Advances on the Synthesis of Ten-Membered Nitrogen Heterocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 420-442.
[2]	Erjun Hao, Xiaobo Ding, Kexin Wang, Honghao Zhou, Qiliang Yang, Lei Shi. Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4057-4074.
[3]	Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.
[4]	Xinyuan Zhang, Li Lin, Jing Li, Shiyu Duan, Yuhang Long, Jiahong Li. Recent Progress in the Synthesis of Medium-Sized Ring and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1878-1887.
[5]	Liu Wenzhu, Dou Lijuan, Mu Weihua. Recent Progress on[3+2] Ring-Expansion Reaction of Cyclopropane with Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1150-1176.
[6]	Pun Sai Ho, Miao Qian. Introduction of Eight-Membered Rings to Polycyclic Arenes by Ring Expansion [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3347-3353.
[7]	Hu Hui, Hu Xiaoping, Chen Ming, Sun Ning, Liu Yuanhong. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds [J]. Chin. J. Org. Chem., 2018, 38(1): 190-199.
[8]	Zhuo Qingde, Wang Tongdao, Zhou Xiaoxi, Zhang Hong. Progresses of Ring Expansion Reaction of Small Transitional Metallacyclic Compounds [J]. Chin. J. Org. Chem., 2014, 34(8): 1471-1486.
[9]	Liu, Junhui ; Zhang, Wenxiong; Xi, Zhenfeng*. Synthesis and Reactivity of Four-Membered Silacycles [J]. Chin. J. Org. Chem., 2009, 29(04): 491-503.
[10]	GONG Wei-Tao, LI Xin-Cheng, NING Gui-Ling, LIN Yuan. Ring-Enlargement Oxidation of Polyphenyl Substituted Cyclopentadiene Promoted by Perchloric Acid [J]. Chinese Journal of Organic Chemistry, 2004, 24(11): 1475-1477.
[11]	RONG GUOBIN;ZHAO ZHONGDE. The bredt's rule and bridgehead bicycloalkenes [J]. Chin. J. Org. Chem., 1992, 12(2): 139-145.

锆路易斯酸催化的环状β-二羰基化合物的de Mayo型扩环反应

Zirconium Lewis Acid-Catalyzed de Mayo-Type Ring Expansion of Cyclic β-Dicarbonyls

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 11

Recommended Articles

Metrics

Comments