Enantioselective Synthesis ofα-Alkenylatedγ-Lactam Enabled by Ni-Catalyzed 1,4-Arylcarbamoylation of 1,3-Dienes  

作　　者：Feng He Liting Hou Xianqing Wu Haojie Ding Jingping Qu Yifeng Chen 

机构地区：[1]Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering,Feringa Nobel Prize Scientist Joint Research Center,Frontiers Science Center for Materiobiology and Dynamic Chemistry,School of Chemistry and Molecular Engineering,East China University of Science and Technology,Shanghai 200237

出　　处：《CCS Chemistry》2023年第2期341-349,共9页中国化学会会刊（英文）

基　　金：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);the Fundamental Research Funds for the Central Universities and the China Postdoctoral Science Foundation(grant no.2021M701197).

摘　　要：The facile construction of chiral quaternaryα-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 nickelcatalyzed asymmetric 1,4-arylcarbamoylation of unactivated 1,3-dienes tethered on carbamoyl fluoride with readily available arylboronic acids,providing rapid access to the enantioenrichedα-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.

关 键 词：LACTAM NICKEL 1 3-diene enantioselective dicarbofunctionalization quaternary stereogenic center 

分 类 号：O621.3[理学—有机化学]