文献类型：期刊文献

英文题名：Organocatalyzed diastereo- and enantioselective synthesis of N-N atropisomeric isoindolinones bearing central chirality

作者：Li, Xingguang[1];Wang, Xin-Ze[1];Shen, Boming[2,3];Chen, Qian-Yu[1];Xiang, Huijing[4];Yu, Peiyuan[2,3];Liu, Pei-Nian[1,5]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China;[3]Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China;[4]Shanghai Univ, Sch Life Sci, Shanghai 200444, Peoples R China;[5]China Pharmaceut Univ, Sch Pharm, State Key Lab Nat Med, Nanjing 210009, Peoples R China

年份：2025

卷号：16

期号：1

外文期刊名：NATURE COMMUNICATIONS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001422743500014)】；

基金：This work was supported by the National Natural Science Foundation of China (22201073 to X.L., 21925201 to P.-N.L., 22161160319 to P.-N.L., T2322018 to H.X., 22171130 to P.Y., 32171391 to H.X.) and the Fundamental Research Funds for the Central Universities. We thank the Research Center of Analysis and Test of East China University of Science and Technology for help in the characterization. P.Y. acknowledges Shenzhen Science and Technology Program (KQTD20210811090112004) for financial support. Computational work was supported by the Center for Computational Science and Engineering and the CHEM High-Performance Supercomputer Cluster (CHEM-HPC) of the Department of Chemistry, Southern University of Science and Technology.

语种：英文

摘要：Methods for catalytically constructing of N-N axially chiral scaffolds have garnered significant attention since such compounds are widely present in natural products, bioactive molecules, and organic materials. Herein, we report a highly diastereoselective and enantioselective organocatalyzed [4 + 1] annulation method for synthesizing diverse valuable isoindolinones that possessing N-N axial and central chiralities. This methodology uses a chiral phosphoric acid as a bifunctional catalyst to promote a cascade sequence involving two nucleophilic additions, dehydration, and dearomatization processes. Control experiments and DFT calculations revealed a possible mechanism in which the stereoselectivity-determining step is likely to involve the irreversible formation of a hydroxy biaryl intermediate. Additionally, preliminary biological activity studies showed that some of these N-N axially chiral isoindolinones have potential in suppressing tumor-cell proliferation.