文献类型：期刊文献

英文题名：Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes

作者：Jin, Qaowen[1];Zheng, Changwu[2];Zhao, Gang[2];Zou, Gang[1]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

年份：2017

卷号：82

期号：9

起止页码：4840

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20171903655175);WOS:【SCI-EXPANDED(收录号:WOS:000401044700033)，CCR-EXPANDED(收录号:WOS:000401044700033)】；

基金：Financial support from Chinese Academy of Sciences (XDB 20020100) and the National Natural Science Foundation of China (Nos. 21272247, 21572247, 21290184) is gratefully acknowledged.

语种：英文

外文关键词：Salts - Catalysis - Stereoselectivity

摘要：A highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to beta-haloalkene ketones/esters catalyzed by readily available chiral bifunctional quaternary ammonium salts is reported. This reaction provides efficient access to a range of 2-oxoindole derivatives bearing a thermodynamically unstable Z-olefin structure and a chiral quaternary carbon center in high yields (up to 90%) and with good to high stereoselectivities (up to >19:1 Z/E and 91% ee) under mild conditions.