LICP OpenIR  > 羰基合成与选择氧化国家重点实验室(OSSO)
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
DepartmentOSSO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 PublicationTetrahedron
ISSN0040-4020
Volume72Issue: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.

KeywordCycloaddition Asymmetric Catalysis Sliver Azomethine Ylide Phosphine Atropisomer
Subject Area物理化学与绿色催化
DOI10.1016/j.tet.2015.09.068
Funding Organizationthe National Natural Science Founder of China (No. 21173064;21133011;21472031);Zhejiang Provincial Natural Science Foundation of China (LR14B030001)
Indexed BySCI
If2.126
Language英语
Funding Project均相催化研究组
compositor第一作者单位
Citation statistics
Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://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 AuthorXia CG(夏春谷); Xu LW(徐利文)
Affiliation1.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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