文献类型：期刊文献

英文题名：Catalytic Asymmetric Diarylation of Internal Acyclic Styrenes and Enamides

作者：Xi, Yang[1,2];Huang, Wenyi[1,2];Wang, Chenchen[1,2];Ding, Haojie[1,2];Xia, Tingting[1,2];Wu, Licheng[1,2];Fang, Ke[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2]

机构：[1]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn,Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, Shanghai 200237, Peoples R China

年份：2022

卷号：144

期号：18

起止页码：8389

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20222012119447);WOS:【SCI-EXPANDED(收录号:WOS:000799180800048)，CCR-EXPANDED(收录号:WOS:000799180800048)】；

基金：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), Program of Introducing Talents of Discipline to Universities (B16017), and 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：Olefins - Styrene

摘要：Enantioselective transformations of olefins are among the most important strategies for the asymmetric synthesis of organic compounds. Chemo-, diastereo-, and stereoselective control of reactions with internal acyclic alkenes for the construction of functionalized acyclic alkanes still remain a persistent challenge. Here, we report a palladium- catalyzed asymmetric regiodivergent Heck-type diarylation of internal acyclic alkenes. The 1,2-diarylation of two accessible acyclic alkenes, cinnamyl carbamates and enamides with diazonium salts and aromatic boronic acids, furnishes products containing vicinal stereogenic centers via the stereospecific formation of carbonyl coordination-assisted transient palladacycles. Moreover, the asymmetric migratory diarylation of enamides enables the formation of incontiguous stereocenters by an interrupted diastereoselective 1,3-chain-walking process. This protocol streamlines access to highly functionalized multisubstituted enantioenriched carbamates and amine derivatives which are embedded in the key biologically active motifs.