文献类型：期刊文献

英文题名：Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams

作者：Zhang, Chenhuan[1,2];Wu, Xianqing[1,2];Xia, Tingting[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2]

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, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]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, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2022

卷号：13

期号：1

外文期刊名：NATURE COMMUNICATIONS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000867457000029)】；

基金：This work was sponsored 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) and the Program of Introducing Talents of Discipline to Universities (B16017), and the Fundamental Research Funds for the Central Universities (222201717003) and the China Postdoctoral Science Foundation (2021M701197). The authors thank Research Center of Analysis and Test of East China University of Science and Technology for the help on NMR analysis.

语种：英文

摘要：Nitrogen-based heterocycles have aroused widespread interest due to their reoccurrence in many pharmaceuticals. Amongst these motifs, the enantioenriched lactams are the ubiquitous scaffolds found in myriad biologically active natural products and drugs. Recently, the transition metal-catalyzed asymmetric carbamoylation has been widely employed as a straightforward arsenal for chiral lactam architecture synthesis, including beta-lactam and gamma-lactam. However, despite the extensive efforts, there still remains no protocol to accomplish the related delta-lactam synthesis. In this manuscript, the Ni-catalyzed enantioselective carbamoylation of unactivated alkenes by the leverage of reductive dicarbofunctionalization strategy allows for the expedient access to two types of mostly common six-membered lactams: 3,4-dihydroquinolinones and 2-piperidinone in high yield and enantioselectivity. This protocol features with good functional group tolerance, as well as broad substrate scope. The newly developed chiral 8-Quinox skeleton ligand is the key parameter for this transformation, which significantly enhances the reactivity and enantioselectivity.