文献类型：期刊文献

英文题名：Pd(0)-Catalyzed Diastereoselective and Enantioselective Intermolecular Heck-Miyaura Borylation of Internal Enamides for the β-Aminoboronate Ester Synthesis

作者：Wang, Chenchen[1,2];Xi, Yang[1,2];Xia, Tingting[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2]

机构：[1]East China Univ Sci & Technol, 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, Shanghai 200237, Peoples R China

年份：2023

卷号：14

期号：1

起止页码：418

外文期刊名：ACS CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001137564700001)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 22171079, 22371071), Natural Science Foundation of Shanghai (No. 21ZR1480400), Shanghai Rising-Star Program (No. 20QA1402300), Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (No. B16017), the China Postdoctoral Science Foundation (No. 2023TQ0118) and the 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 and HRMS analysis.

语种：英文

外文关键词：asymmetric catalysis; cross-coupling reaction; vicinal stereocenters; palladium; organoboron chemistry

摘要：Miyaura borylation is widely recognized as one of the most reliable methods for constructing an organoboron compound. Reported herein is Pd(0)-catalyzed asymmetric three-component Heck-Miyaura borylation with the interception of internal olefin, aryldiazonium salt, and diboron reagent. This Heck-triggered borylation protocol proceeds in a highly chemoselective, diastereoselective, and enantioselective manner, thus allowing the expedient construction of 1,2-diaryl substituted beta-aminoboronate esters derivatives with vicinal stereogenic centers. The versatility of the resulting benzylic boronic esters allows for their further transformation to more-intricate chiral amines.