Citation: Wei Yang, Zhendong Yang, Long Chen, Yican Lu, Cefei Zhang, Zhishan Su, Xiaohua Liu, Xiaoming Feng. Chiral nickel(Ⅱ) complex catalyzed asymmetric (3 + 2) cycloaddition of α-diazo pyrazoleamides with 2-siloxy-1-alkenes[J]. Chinese Chemical Letters, ;2023, 34(4): 107791. doi: 10.1016/j.cclet.2022.107791 shu

Chiral nickel(Ⅱ) complex catalyzed asymmetric (3 + 2) cycloaddition of α-diazo pyrazoleamides with 2-siloxy-1-alkenes

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

liuxh@scu.edu.cn

xmfeng@scu.edu.cn

Received Date: 29 June 2022
Revised Date: 23 August 2022
Accepted Date: 29 August 2022
Available Online: 31 August 2022

Figures(5)

A highly efficient asymmetric (3 + 2) cycloaddition of α-diazo pyrazoleamides with silyl enol ethers was realized by employing a chiral N, N'-dioxide-Ni(Ⅱ) complex catalyst. The process includes the formation of chiral nickel carbenoid intermediate and the following enantioselective cycloaddition reaction. The desired dihydrofuran O, O-acetal derivatives were obtained in good yields (up to 90%) with high enantioselectivity (up to 99% ee) under mild reaction conditions within short reaction time. On the basis of the determination of the catalyst structure, a possible transition state mode was proposed.
- Asymmetric catalysis,
- (3 + 2) Cycloaddition,
- Chiral N, N'-dioxide,
- Silyl enol ether,
- α-Diazo pyrazoleamide,
- Dihydrofuran
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