N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides | |
Department | OSSO国家重点实验室 |
Bo XF(柏惺峰)1,2; Zhang, Jin2; Xia CG(夏春谷)1; Xu, Jian-Xing2; Xu LW(徐利文)1,2; Xia CG(夏春谷); Xu LW(徐利文) | |
2016 | |
Source Publication | Tetrahedron |
ISSN | 0040-4020 |
Volume | 72Issue:21Pages:2690-2699 |
Abstract | Simple modifications of our novel ligand (Xing-Phos) were presented in this work, and a series of aromatic tertiary amide derived non-biaryl atropisomers were successfully synthesized in good yields. In addition, it was found that the multifunctional aromatic tertiary amide derived non-biaryl atropisomers exhibited an excellent endo-selectivity in the silver-catalyzed [3+2]-cycloaddition of azomethine ylides with N-aromatic maleimide. And especially, good to high levels of enantioselectivity (up to 98% ee) was obtained with a wide range of substrates in the presence of syn-(R, RS)-2a (Xing-Phos). Furthermore, on the basis of the experimental data, it was demonstrated that a trace amount of water play an important role in the enhancement of enantioselectivity. |
Keyword | Cycloaddition Asymmetric Catalysis Sliver Azomethine Ylide Phosphine Atropisomer |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1016/j.tet.2015.09.068 |
Funding Organization | the National Natural Science Founder of China (No. 21173064;21133011;21472031);Zhejiang Provincial Natural Science Foundation of China (LR14B030001) |
Indexed By | SCI |
If | 2.126 |
Language | 英语 |
Funding Project | 均相催化研究组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/23816 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Xia CG(夏春谷); Xu LW(徐利文) |
Affiliation | 1.State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (CAS), and University of the Chinese Academy of Sciences, PR China 2.Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou 311121, PR China |
Recommended Citation GB/T 7714 | Bo XF,Zhang, Jin,Xia CG,et al. N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides[J]. Tetrahedron,2016,72(21):2690-2699. |
APA | Bo XF.,Zhang, Jin.,Xia CG.,Xu, Jian-Xing.,Xu LW.,...&徐利文.(2016).N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides.Tetrahedron,72(21),2690-2699. |
MLA | Bo XF,et al."N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides".Tetrahedron 72.21(2016):2690-2699. |
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