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题名: Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity
作者: Wang, H;  Liu, XJ;  Xia, HA;  Liu, P;  Gao, JB;  Ying, PL;  Xiao, JL;  Li, C
关键词: configuration ;  Diels-Alder reactions ;  heterogeneous catalysis ;  hydrogen bonding ;  Lewis acids
刊名: TETRAHEDRON
发表日期: 2006-01-30
DOI: 10.1016/j.tet.2005.09.148
卷: 62, 期:5, 页:1025-1032
收录类别: SCI ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: Chiral bis(oxazoline) complexes of Cu(II), Zn(II) and Mg(II) have been immobilized on silica support via hydrogen-bonding interactions. Up to 93% ee is obtained in the Diels-Alder reaction between 3-((E)-2-butenoyl)-1,3-oxazolin-2-one and cyclopentadiene at room temperature with the heterogeneous bis(oxazoline) complexes, and the catalysts can be recycled without losing enantioselectivity. Experimental and theoretical studies show that the reversal of the absolute product configuration upon immobilization of the PhBOX-Cu(II) catalyst is triggered by the anion dissociation from Cu(II) onto the surface of the support. (c) 2005 Elsevier Ltd. All rights reserved.
关键词[WOS]: BIS(OXAZOLINE) COPPER(II) COMPLEXES ;  CHIRAL LEWIS-ACIDS ;  ENE REACTIONS ;  CYCLOPROPANATION REACTIONS ;  ADDITION-REACTIONS ;  CARBONYL-ENE ;  SILICA ;  IMMOBILIZATION ;  ENANTIOMERS ;  SURFACES
语种: 英语
WOS记录号: WOS:000234783200027
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140284
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
3.Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

Recommended Citation:
Wang, H,Liu, XJ,Xia, HA,et al. Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity[J]. TETRAHEDRON,2006,62(5):1025-1032.
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