文献类型：期刊文献

英文题名：Enantioselective Synthesis of α-Alkenylated γ-Lactam Enabled by Ni-Catalyzed 1,4-Arylcarbamoylation of 1,3-Dienes

作者：He, Feng[1];Hou, Liting[1];Wu, Xianqing[1];Ding, Haojie[1];Qu, Jingping[1];Chen, Yifeng[1]

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

年份：2023

卷号：5

期号：2

起止页码：341

外文期刊名：CCS CHEMISTRY

收录：WOS:【ESCI(收录号:WOS:001072569400007)】；

基金：This work was supported by National Natural Science Foundation of China (grant no. 22171079), the Natural Science Foundation of Shanghai (grant no. 21ZR1480400), the Shanghai Rising-Star Program (grant no. 20QA1402300), the Shanghai Municipal Science and Technology Major Project (grant no. 2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (grant no. B16017), and the Fundamental Research Funds for the Central Universities and the China Postdoctoral Science Foundation (grant no. 2021M701197). 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：lactam; nickel; 1, 3-diene; enantioselective dicarbofunctionalization; quaternary stereogenic center

摘要：The facile construction of chiral quaternary alpha-alkenylated pyrrolidinones is a long-term challenge in organic synthesis. The asymmetric difunctionalization of 1,3-dienes represents the most compelling tool for assembling alkenylated compounds by regioselective 1,2- or 1,4-difunctionalization. Nevertheless, the manipulation of unactivated 1,3-dienes to forge the quarternary stereogenic center still remains largely underdeveloped. Herein, we disclose a nickel-catalyzed asymmetric 1,4-arylcarbamoylation of unactivated 1,3-dienes tethered on carbamoyl fluoride with readily available arylboronic acids, providing rapid access to the enantioenriched alpha-alkenylated pyrrolidinones bearing the quaternary stereogenic center in high yields with broad functional group tolerance. Moreover, this chiral ligand-controlled asymmetric transformation overcomes the intrinsic substrate control with a preexisting chiral center. [GRAPHICS] .