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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
KeywordConfiguration Diels-alder Reactions Heterogeneous Catalysis Hydrogen Bonding Lewis Acids
Source PublicationTETRAHEDRON
2006-01-30
DOI10.1016/j.tet.2005.09.148
Volume62Issue:5Pages:1025-1032
Indexed BySCI ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordBIS(OXAZOLINE) COPPER(II) COMPLEXES ; CHIRAL LEWIS-ACIDS ; ENE REACTIONS ; CYCLOPROPANATION REACTIONS ; ADDITION-REACTIONS ; CARBONYL-ENE ; SILICA ; IMMOBILIZATION ; ENANTIOMERS ; SURFACES
AbstractChiral 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.
Language英语
WOS IDWOS:000234783200027
Citation statistics
Cited Times:36[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/140284
Collection中国科学院大连化学物理研究所
Affiliation1.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
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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