Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N-4 Ligands Derived from Rigid Chiral Diamines | |
Department | OSSO国家重点实验室 |
Chen, Xiangning1; Gao, Bao2; Su YJ(苏毅进)1; Huang HM(黄汉民)1,2; Huang HM(黄汉民) | |
2017 | |
Source Publication | Advanced Synthesis & Catalysis |
ISSN | 1615-4150 |
Volume | 359Issue:15Pages:2535-2541 |
Abstract | A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. |
Keyword | Alkenes Chiral N-4 Ligands Enantioselective Epoxidation Hydrogen Peroxide Manganese |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1002/adsc.201700541 |
Funding Organization | CAS Interdisciplinary Innovation Team;the National Natural Science Foundation of China (21672199;21172226);the Anhui provincial Natural Science Foundation (1708085MB28) |
Indexed By | SCI |
If | 5.646 |
Language | 英语 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/22427 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Huang HM(黄汉民) |
Affiliation | 1.State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PeopleQs Republic of China 2.Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei 230026, PeopleQs Republic of China |
Recommended Citation GB/T 7714 | Chen, Xiangning,Gao, Bao,Su YJ,et al. Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N-4 Ligands Derived from Rigid Chiral Diamines[J]. Advanced Synthesis & Catalysis,2017,359(15):2535-2541. |
APA | Chen, Xiangning,Gao, Bao,Su YJ,Huang HM,&黄汉民.(2017).Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N-4 Ligands Derived from Rigid Chiral Diamines.Advanced Synthesis & Catalysis,359(15),2535-2541. |
MLA | Chen, Xiangning,et al."Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N-4 Ligands Derived from Rigid Chiral Diamines".Advanced Synthesis & Catalysis 359.15(2017):2535-2541. |
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Adv.Synth. Catal. 20(1343KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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