文献类型：期刊文献

英文题名：Asymmetric synthesis of 3-benzyl and allyl isoindolinones by Pd-catalyzed dicarbofunctionalization of 1,1-disubstituted enamides

作者：Huang, Wenyi[1,2];Shrestha, Mohini[1,2];Wang, Chenchen[1,2];Fang, Ke[1,2];Teng, Yaxin[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 Mat & Dynam Chem, Key Lab Adv Mat,Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Mat & Dynam Chem, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2021

卷号：8

期号：15

起止页码：4106

外文期刊名：ORGANIC CHEMISTRY FRONTIERS

收录：;EI(收录号：20213110713987);WOS:【SCI-EXPANDED(收录号:WOS:000656555600001)，CCR-EXPANDED(收录号:WOS:000656555600001)】；

基金：This work was supported by NSFC/China (21702060), the Shanghai Rising-Star Program, the Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03) and the Program of Introducing Talents of Discipline to Universities (B16017). The authors thank the 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：Enantioselectivity - Catalysis

摘要：Enantioenriched isoindolinones represent a valuable heterocycle motif, widely found in pharmaceuticals and biologically active natural products. We herein report a palladium-catalyzed asymmetric synthesis of 3,3-disubstituted isoindolinones via the tandem Heck/Suzuki coupling of 1,1-disubstituted enamides with aryl/alkenyl boronic acids under mild reaction conditions. This reaction exhibits both broad functional group tolerance and high enantioselectivity. We report the first dicarbo-functionalization of 1,1-disubstituted enamides to generate amide derivatives bearing quaternary stereocenters. Finally, the synthetic utility of this protocol is demonstrated by the expedient synthesis of the PI3K-delta inhibitor precursor.