文献类型：期刊文献

英文题名：Diastereo- and Enantioselective Michael Addition of 3-Substituted Oxindoles to Trifluoromethyl-Substituted Nitro Olefins Catalyzed by a Cinchona-Alkaloid-Derived Squaramide

作者：Zhao, Mei-Xin[1,2];Ji, Fei-Hu[1,2];Zhao, Xiao-Li[3];Han, Ze-Zheng[1,2];Shi, Min[1,2,4]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

年份：2014

卷号：2014

期号：3

起止页码：644

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000330801400021)，CCR-EXPANDED(收录号:WOS:000330801400021)】；

基金：The authors are grateful for financial support from the National Natural Science Foundation of China (NSFC) (grant numbers 20772030, 21072056, 21272067), the Fundamental Research Funds for the Central Universities, the Scientific Research Foundation for the Returned Overseas Chinese Scholars, and the State Education Ministry, P.R. China.

语种：英文

外文关键词：Organocatalysis; Michael addition; Heterocycles; Alkaloids; Fluorine

摘要：Highly efficient diastereo- and enantioselective Michael addition reactions between 3-substituted oxindoles and trifluoromethylated nitro olefins catalyzed by a quinine-derived squaramide have been investigated. The corresponding adducts, each bearing a chiral tertiary carbon center attached to a trifluoromethyl group and adjacent to a quaternary stereocenter at the C3 position of the oxindole, were obtained in good to excellent yields (up to 99%) and with high diastereoselectivities (up to >20:1 dr) and excellent enantioselectivities (up to 99% ee).