Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne-azide click cycloaddition: substrate scope and mechanism | |
Department | OSSO国家重点实验室 |
Chen, Mu-Yi1; Song, Tao1; Zheng, Zhan-Jiang1; Xu, Zheng1; Cui, Yu-Ming1; Xu LW(徐利文)1,2; Xu LW(徐利文) | |
2016 | |
Source Publication | RSC Advances |
ISSN | 2046-2069 |
Volume | 6Issue:63Pages:58698-58708 |
Abstract | It was found that the catalytic Huisgen cycloaddition reaction of succinimide-derived bisalkynes with azides resulted in useful succinimide-derived triazoles bearing quaternary carbon-stereogenic centers with good to excellent yields as well as good chemoselectivity and moderate to high enantioselectivities (up to 97% ee), in which the CuF2/Tao-Phos complex was proved to be an effective bimetallic catalyst in the presence of triethylamine. The mechanistic studies based on the effect of reaction parameters on stereoselectivity as well as ESI-MS analysis suggested that our ligand (Tao-Phos) and related binuclear copper centers play a crucial role in this asymmetric click chemistry because of the strong catalyst–substrate interaction with the aid of a possibly in situ formed binuclear or multinuclear copper-based transition state. This work not only provides a new example of a Cu(II)-mediated asymmetric AAC reaction involving chelating base and azides, but also suggests the significance of binuclear copper species in catalytic asymmetric click reactions with two copper center-involved enantioselective inductions. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1039/c6ra13687g |
Funding Organization | the National Natural Science Founder of China (No. 51303043;21472031;21503060);Zhejiang Provincial Natural Science Foundation of China (LR14B030001);Science and Technology Department of Zhejiang Province (2015C31138);Hangzhou Science and Technology Bureau of China (20140432B04) |
Indexed By | SCI |
If | 3.108 |
Language | 英语 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/20193 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Xu LW(徐利文) |
Affiliation | 1.Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
Recommended Citation GB/T 7714 | Chen, Mu-Yi,Song, Tao,Zheng, Zhan-Jiang,et al. Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne-azide click cycloaddition: substrate scope and mechanism[J]. RSC Advances,2016,6(63):58698-58708. |
APA | Chen, Mu-Yi.,Song, Tao.,Zheng, Zhan-Jiang.,Xu, Zheng.,Cui, Yu-Ming.,...&徐利文.(2016).Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne-azide click cycloaddition: substrate scope and mechanism.RSC Advances,6(63),58698-58708. |
MLA | Chen, Mu-Yi,et al."Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne-azide click cycloaddition: substrate scope and mechanism".RSC Advances 6.63(2016):58698-58708. |
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