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

作　　者：Zhenni Zhao Zhi Ou Subarna Jyoti Kalita Feng Cheng Qian Huang Yangyi Gu Yuhao Wang Yan Zhao Yiyong Huang 

机构地区：[1]Department of Chemistry,School of Chemistry,Chemical Engineering and Life Science,Wuhan University of Technology,Wuhan 430070,China [2]State Key Laboratory of Silicate Materials for Architectures,Wuhan University of Technology,Wuhan 430070,China

出　　处：《Chinese Chemical Letters》2022年第6期3012-3016,共5页中国化学快报（英文版）

基　　金：the financial support for this investigation from the National Natural Science Foundation of China(Nos.21772151,22072111);the Fundamental Research Funds for Central Universities(No.WUT:2021IVA121).

摘　　要：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 regioand 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.

关 键 词：Stereoconvergent 1 3-Dipolar cycloaddition ISOXAZOLINE PYRAZOLINE TRIFLUOROMETHYL 

分 类 号：O621.25[理学—有机化学]