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Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity
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
2006-01-30
DOI10.1016/j.tet.2005.09.148
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
关键词[WOS]BIS(OXAZOLINE) COPPER(II) COMPLEXES ; CHIRAL LEWIS-ACIDS ; ENE REACTIONS ; CYCLOPROPANATION REACTIONS ; ADDITION-REACTIONS ; CARBONYL-ENE ; SILICA ; IMMOBILIZATION ; ENANTIOMERS ; SURFACES
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.
语种英语
WOS记录号WOS:000234783200027
引用统计
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/140284
专题中国科学院大连化学物理研究所
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
推荐引用方式
GB/T 7714
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.
APA Wang, H.,Liu, XJ.,Xia, HA.,Liu, P.,Gao, JB.,...&Li, C.(2006).Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity.TETRAHEDRON,62(5),1025-1032.
MLA Wang, H,et al."Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity".TETRAHEDRON 62.5(2006):1025-1032.
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