文献类型：期刊文献

英文题名：Enhanced Pyridine-Oxazoline Ligand-Enabled Pd(II)-Catalyzed Aminoacetoxylation of Alkenes for the Asymmetric Synthesis of Biaryl-Bridged 7-Membered N-Heterocycles and Atropisomers

作者：Guo, Beibei[1,2];Yan, Xiaoyang[3,4];Wang, Zicong[3,4];Shen, Chen[1,2];Chen, Weifu[1,2];Cen, Shouyi[1,2];Peng, Qian[3,4,5];Zhang, Zhipeng[1,2]

机构：[1]East China Univ Sci & Technol, 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;[3]Nankai Univ, Frontiers Sci Ctr New Organ Matter, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China;[4]Nankai Univ, Coll Chem, Tianjin Key Lab Biosensing & Mol Recognit, Tianjin 300071, Peoples R China;[5]Haihe Lab Sustainable Chem Transformat, Tianjin 300192, Peoples R China

年份：2025

卷号：147

期号：15

起止页码：12614

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20251418177556);WOS:【SCI-EXPANDED(收录号:WOS:001456934000001)，CCR-EXPANDED(收录号:WOS:001456934000001)】；

基金：We thank the Research Center of Analysis and Test, East China University of Science and Technology, for their help with the characterization. We thank Prof. Yuan-Yuan Zhu (HFUT) for the help with single-crystal X-ray diffraction and structure analysis. We acknowledge the National Natural Science Foundation of China (22371072 and 92156017), the Natural Science Foundation of Shanghai (24ZR1415000), the Natural Science Foundation of Tianjin (24JCZDJC00750), the Fundamental Research Funds for the Central Universities (222201717003, JKVJ1241010, SLJ13233303, and YJ0142225), the Science and Technology Commission of Shanghai Municipality (24DX1400200), the Haihe Laboratory of Sustainable Chemical Transformation of Tianjin (24HHWCSS00019), the Program of Introducing Talents of Discipline to Universities (B16017), the "Frontiers Science Center for New Organic Matter", Nankai University (63181206), and the Shanghai Postdoctoral Excellence Program (2022145) for their generous financial support.

语种：英文

外文关键词：Catalysis - Chitin - Enantioselectivity - Hydroxylation - Pyridine

摘要：A new class of binaphthyl unit-enhanced pyridine-oxazoline ligands was developed to promote the Pd-catalyzed enantioselective intramolecular 7-exo aminoacetoxylation of unactivated biaryl alkenes. Biaryl-bridged 7-membered N-heterocycles bearing a chiral center were obtained in good yields with excellent enantioselectivities (up to 99:1 er). Computational investigations on a series of biaryl-bridged 7-membered rings provided insights into the rotational barrier of the potentially chiral biaryl unit by the substituent effect including the heteroatom, the protecting group, and the chiral center. The kinetic resolution of racemic axially chiral biaryls via intramolecular enantioselective aminoacetoxylation of alkenes has also been achieved, affording previously inaccessible biaryl-bridged 7-membered N-heterocycles bearing both a chiral center and a chiral axis, as well as axially chiral biaryl amino alcohols.