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

被引：1

作者：

Zhenni Zhao ^{[1
]}

Zhi Ou ^{[1
]}

Subarna Jyoti Kalita ^{[1
]}

Feng Cheng ^{[1
]}

Qian Huang ^{[1
]}

Yangyi Gu ^{[1
]}

Yuhao Wang ^{[1
]}

Yan Zhao ^{[2
]}

Yiyong Huang ^{[1
]}

机构：

[1] Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology

[2] State Key Laboratory of Silicate Materials for Architectures, Wuhan University of Technology

来源：

Chinese Chemical Letters | 2022年 / 06期

基金：

中国国家自然科学基金;

关键词：

D O I：

暂无

中图分类号：

O621.25 [];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：3012 / 3016

页数：5

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