文献类型：期刊文献

英文题名：Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam

作者：Wu, Xianqing[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Frontiers Sci Ctr Materiobiol & Dynam Chem, Key Lab Adv Mat,Feringa Nobel Prize Scientist Joi, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Frontiers Sci Ctr Materiobiol & Dynam Chem, Joint Int Res Lab Precis Chem & Mol Engn,Feringa, Shanghai 200237, Peoples R China

年份：2020

卷号：142

期号：37

起止页码：15654

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20204209355381);WOS:【SCI-EXPANDED(收录号:WOS:000573374400005)，CCR-EXPANDED(收录号:WOS:000573374400005)】；

基金：This work is dedicated to the 70th anniversary of the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. This work was supported by NSFC/China (21421004, 21702060), Shanghai Rising-Star Program, Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03) and the Program of Introducing Talents of Discipline to Universities (B16017), and the Fundamental Research Funds for the Central Universities. Y.C. thanks Prof. Zhipeng Zhang (ECUST) for sharing the instruments and Prof. Timothy Newhouse (Yale University) for helpful discussion. The authors thank Research Center of Analysis and Test of East China University of Science and Technology for the help with NMR analysis.

语种：英文

外文关键词：Chelation - Chlorine compounds - Catalysis - Cyclization - Enantioselectivity - Nickel - Scaffolds

摘要：Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral a-alkylated pyrrolidinone with broad substrate scope and high enantiomeric excess. The current art of synthesis still remains challenging on the enantioselective alpha-monoalkylation of pyrrolidinones. The newly designed chiral 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining the reactivity and enantioselectivity to ensure the reductive cyclization of monosubstituted alkenes for unprecedented synthesis of chiral non-aromatic heterocycles.