Citation: Fangqing Zhang, Yu Wang, Zhenda Tan, Yangbin Liu, Lijuan Song, Xiaoming Feng. Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers[J]. Chinese Chemical Letters, ;2025, 36(7): 110581. doi: 10.1016/j.cclet.2024.110581 shu

Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers

Fangqing Zhang ^{a, b, 1} ,
Yu Wang ^{c, 1} ,
Zhenda Tan ^b ,
Yangbin Liu ^{a, b, *,} ,
Lijuan Song ^{c, *,} ,
Xiaoming Feng ^{b, d, *,}

a.
State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China
b.
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China
c.
School of Science, Harbin Institute of Technology, Shenzhen 518055, China
d.
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

liuyb@szbl.ac.cn

songlijuan@hit.edu.cn

xmfeng@scu.edu.cn

Received Date: 14 August 2024
Revised Date: 16 October 2024
Accepted Date: 23 October 2024
Available Online: 28 October 2024

Figures(5)

Chiral aryl cyclohex-3-en ether scaffold is widely present in bioactive natural products and drugs. The exploitation of efficient and enantioselective methods for the construction of aryl cyclohex-3-en ether scaffold is significant. Herein we disclose a chiral N,N’-dioxide/Lewis acid complex-catalyzed asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction using electron-deficient 3-carboalkoxyl-2-pyrones and less electron-enriched aryl enol ethers as reactants. A wide range of non- and 1,2-disubstituted acyclic aryl enol ethers are applicable to deliver diverse chiral bridged bicyclic lactones in high yields and stereoselectivities (up to 96% yield, > 20:1 dr, 97:3 er). The bridged bicyclic lactone core can be easily converted into chiral aryl cyclohex-3-en ether scaffold. Notably, DFT calculations revealed a stepwise and endo mechanism to explain the high enantioselectivity controlled by the cooperative effect of the steric factors and the dispersion interactions between ligands and enol ethers.
- Asymmetric IEDDA reaction,
- Aryl cyclohex-3-en ether scaffold,
- 2-Pyrone,
- Chiral Lewis acid complex,
- Chiral bridged bicyclic lactones
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