文献类型：期刊文献

英文题名：Axially Chiral Phenanthroline Ligand-Enabled Pd-Catalyzed Asymmetric Amination and Alkylation of Aryl-Substituted Morita-Baylis-Hillman Adducts

作者：Shen, Ahui[1,2];Bao, Rongrong[1,2];Shen, Chen[1,2];Cen, Shouyi[1,2];Zhang, Zhipeng[1,2]

机构：[1]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Key Lab Adv Mat, 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：2024

卷号：26

期号：50

起止页码：10671

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001372880700001)，CCR-EXPANDED(收录号:WOS:001372880700001)】；

基金：We thank the Research Center of Analysis and Test, East China University of Science and Technology for the help on the characterization. We appreciate the valuable discussion of this work with Prof. Kuiling Ding, Prof. Zhaobin Han, and Prof. Xiaoming Wang at SIOC. We acknowledge the National Natural Science Foundation of China (22371072), the Fundamental Research Funds for the Central Universities (222201717003, JKVJ1241010, JKJ01231652, SLJ13233303, and YJ0142225), Shanghai Municipal Science and Technology Major Project (2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (B16017) and the "Thousand Plan" Youth Program for financial support.

语种：英文

摘要：Highly enantioselective allylic amination and alkylation of racemic sterically hindered aryl-substituted Morita-Baylis-Hillman (MBH) adducts have been achieved by using an in situ formed Pd-catalyst from an axially chiral phenanthroline ligand. This dynamic kinetic asymmetric transformation (DYKAT) is compatible with cyclic and acyclic secondary amines, dialkyl malonates, beta-keto esters, acetylacetone, and malononitrile, affording the corresponding chiral products, such as beta-amino acid esters, in up to 95% yield and with up to a 99:1 enantiomeric ratio.