文献类型：期刊文献

英文题名：Organocatalyzed asymmetric tandem conjugate addition-protonation of isocyanoacetates to 2-chloroacrylonitrile

作者：Yu, Kun-Ming[1,2];Zhu, Hui-Kai[1,2];Zhao, Xiao-Li[3];Shi, Min[1,2,4];Zhao, Mei-Xin[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]East China Normal Univ, Dept Chem, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

年份：2019

卷号：17

期号：3

起止页码：639

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20190406404129);WOS:【SCI-EXPANDED(收录号:WOS:000458578900024)】；

基金：We are grateful for financial support from the National Natural Science Foundation of China (21272067), the Natural Science Foundation of Shanghai (15ZR1411900) and the Fundamental Research Funds for the Central Universities (222201717003).

语种：英文

外文关键词：Positive ions

摘要：An efficient organocatalytic asymmetric tandem conjugate addition-protonation of -substituted isocyanoacetates to 2-chloroacrylonitrile catalyzed by dihydroquinine-derived thiourea has been investigated, affording the corresponding adducts with two non-adjacent tertiary-quaternary stereocenters in excellent yields (up to 99%) along with good to excellent diastereo- and enantioselectivities (up to 20:1 dr, up to 95% ee) under mild conditions. The adduct can also be transformed into chiral -lactam by synthetic transformations.