LICP OpenIR  > 羰基合成与选择氧化国家重点实验室(OSSO)
Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N-4 Ligands Derived from Rigid Chiral Diamines
DepartmentOSSO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 PublicationAdvanced Synthesis & Catalysis
ISSN1615-4150
Volume359Issue: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.

KeywordAlkenes Chiral N-4 Ligands Enantioselective Epoxidation Hydrogen Peroxide Manganese
Subject Area物理化学与绿色催化
DOI10.1002/adsc.201700541
Funding OrganizationCAS Interdisciplinary Innovation Team;the National Natural Science Foundation of China (21672199;21172226);the Anhui provincial Natural Science Foundation (1708085MB28)
Indexed BySCI
If5.646
Language英语
compositor第一作者单位
Citation statistics
Cited Times:26[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://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 AuthorHuang HM(黄汉民)
Affiliation1.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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