Citation: Zhenni Zhao, Zhi Ou, Subarna Jyoti Kalita, Feng Cheng, Qian Huang, Yangyi Gu, Yuhao Wang, Yan Zhao, Yiyong Huang. Stereoconvergent and stepwise 1, 3-dipolar cycloadditions of nitrile oxides and nitrile imines[J]. Chinese Chemical Letters, ;2022, 33(6): 3012-3016. doi: 10.1016/j.cclet.2021.12.006 shu

Stereoconvergent and stepwise 1, 3-dipolar cycloadditions of nitrile oxides and nitrile imines

Zhenni Zhao ^{a, 1} ,
Zhi Ou ^{a, 1} ,
Subarna Jyoti Kalita ^{a, 1} ,
Feng Cheng ^a ,
Qian Huang ^a ,
Yangyi Gu ^a ,
Yuhao Wang ^a ,
Yan Zhao ^b ,
Yiyong Huang ^{a, *,}

a.
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China
b.
State Key Laboratory of Silicate Materials for Architectures, Wuhan University of Technology, Wuhan 430070, China

huangyy@whut.edu.cn

Received Date: 17 October 2021
Revised Date: 17 November 2021
Accepted Date: 1 December 2021
Available Online: 6 December 2021

Figures(6)

The first example of stereoconvergent 1, 3-dipolar cycloaddition of nitrile oxides and nitrile imines with E/Z isomeric mixture of electron-deficient olefins is reported, delivering isoxazolines and pyrazolines bearing two vicinal stereogenic tertiary and trifluoromethylated quaternary carbon centers with perfect regio- and diastereoselectivities. The possibility of concerted cycloaddition/epimerization sequence under basic condition to form the thermodynamically stable diastereomers is excluded through some control experiments and DFT calculations, and a stepwise mechanism is proposed.
- Stereoconvergent,
- 1, 3-Dipolar cycloaddition,
- Isoxazoline,
- Pyrazoline,
- Trifluoromethyl
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