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

作者机构：Department of ChemistrySchool of ChemistryChemical Engineering and Life ScienceWuhan University of TechnologyWuhan 430070China State Key Laboratory of Silicate Materials for ArchitecturesWuhan University of TechnologyWuhan 430070China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2022年第33卷第6期

页      面：3012-3016页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

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) 

主　　题：Stereoconvergent 1,3-Dipolar cycloaddition Isoxazoline Pyrazoline Trifluoromethyl 

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 *** 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.