Stereoconvergent and stepwise 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines
CHINESE CHEMICAL LETTERS(2022)
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 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. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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关键词
Stereoconvergent,1,3-Dipolar cycloaddition,Isoxazoline,Pyrazoline,Trifluoromethyl
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