文献类型：期刊文献

英文题名：Nickel/Quinim Enabled Asymmetric Carbamoyl-Acylation of Unactivated Alkenes

作者：Wu, Xianqing;Li, Haiyan;He, Feng;Qu, Jingping;Chen, Yifeng[1]

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

年份：2023

卷号：41

期号：14

起止页码：1673

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000973116200001)，CCR-EXPANDED(收录号:WOS:000973116200001)】；

基金：Acknowledgement This work was supported by NSFC/China (22171079), Natural Science Foundation of Shanghai (21ZR1480400), Shanghai Rising- Star Program (20QA1402300), Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (B16017), the China Postdoctoral Science Foundation (2021M701197) and the Fundamental Research Funds for the Central Universities. The authors thank the Analysis and Testing Center of East China University of Science and Technology for help with NMR analysis.

语种：英文

外文关键词：Nickel; Quinim ligand; Lactams; Asymmetric catalysis; Alkenes

摘要：Transition metal-catalyzed difunctionalization of tethered alkene has emerged as a prevailing tool for the expedient construction of synthetically valuable cyclic compounds. However, most efforts have been devoted to the reaction of styrene-type substrates due to their rigid scaffold and high reactivity. With respect to the difunctionalization of nonaromatic tethered olefin, especially the mono-substituted alkene, still remains largely underdeveloped. Herein, we disclose a nickel/Quinim complex and TBADT-cocatalyzed asymmetric carbamoyl-acylation of unactivated alkene tethered on nonaromatic carbamoyl chlorides with diverse aldehydes. The reaction exhibits broad substrate scope with good functional group tolerance, as well as high reaction efficiency and enantioselectivity. Both monosubstituted and 1,1-substituted alkenes can work well with either aliphatic or aromatic aldehydes under the current protocol, providing convenient access to an array of medicinally useful chiral ?-lactams derivatives bearing a convertible acyl functionality. This reaction showcases more application possibilities of the chiral Quinim ligand in the future asymmetric catalytic transformations.