文献类型：期刊文献

英文题名：Catalytic Asymmetric Synthesis of Unnatural Axially Chiral Biaryl δ-Amino Acid Derivatives via a Chiral Phenanthroline-Potassium Catalyst-Enabled Dynamic Kinetic Resolution

作者：Cen, Shouyi[1,2];Li, Shan-Shan[1,2];Zhao, Yin[1,2];Zhao, Mei-Xin[1,2];Zhang, Zhipeng[1,2,3]

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 Chemi, Shanghai 200237, Peoples R China;[3]Shanghai Normal Univ, Shanghai Frontiers Sci Ctr Biomimet Catalysis, Shanghai 200234, Peoples R China

年份：2024

卷号：63

期号：36

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20243116798485);WOS:【SCI-EXPANDED(收录号:WOS:001278964800001)，CCR-EXPANDED(收录号:WOS:001278964800001)】；

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 thank Prof. Yuan-Yuan Zhu (HFUT) and Prof. Jie Sun (SIOC) for the help with single crystal X-ray diffraction and structure analysis. We thank Prof. Zhiqian Guo and Dongsheng Lian for the help with measurement of the UV/Vis spectra. We acknowledge the National Natural Science Foundation of China (22371072, 21702059), Fundamental Research Funds for the Central Universities (222201717003, JKVJ1241010, JKJ01231652, JKVJ1231010, SLJ13233303), Shanghai Municipal Science and Technology Major Project (2018SHZDZX03), Program of Introducing Talents of Discipline to Universities (B16017) and the "Thousand Plan" Youth Program for financial support.

语种：英文

外文关键词：axial chirality; amino acid; potassium; chiral phenanthroline; dynamic kinetic resolution

摘要：Axially chiral biaryl delta-amino acids possess significantly different conformational properties and chiral environment from centrally chiral amino acids, therefore, have drawn considerable attention in the fields of synthetic and medicinal chemistry. Herein, a novel chiral phenanthroline-potassium catalyst has been developed by constructing a well-organized axially chiral ligand composed of one 1,10-phenanthroline unit and two axially chiral 1,1 '-bi-2-naphthol (BINOL) units. In the presence of this catalyst, good to excellent yields and enantioselectivities (up to 99 % yield, 98 : 2 er) have been achieved in the ring-opening alcoholytic dynamic kinetic resolution of a variety of biaryl lactams, thereby providing an efficient protocol for catalytic asymmetric synthesis of unnatural axially chiral biaryl delta-amino acid derivatives. A novel axially chiral phenanthroline-potassium catalyst has been developed for the ring-opening alcoholytic dynamic kinetic resolution of a variety of biaryl lactams. Unnatural axially chiral biaryl delta-amino acid derivatives have been synthesized in good to excellent yields and enantioselectivities (up to 99 % yield, 98 : 2 er). image