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Article: Chiral 2-pyridyl alcoholate copper complexes: crystal structures of [bis(2-pyridyl alcoholate)copper(II)] and the use of [(2-pyridyl alcoholate)copper(II)]+ and [(2-pyridyl alcoholate)copper(I)] in asymmetric cyclopropanation of styrene and allylic ox

TitleChiral 2-pyridyl alcoholate copper complexes: crystal structures of [bis(2-pyridyl alcoholate)copper(II)] and the use of [(2-pyridyl alcoholate)copper(II)]+ and [(2-pyridyl alcoholate)copper(I)] in asymmetric cyclopropanation of styrene and allylic ox
Authors
KeywordsCatalyst
Chirality
Crystal structure
Cyclopropanation
Enantioselectivity
Issue Date2004
PublisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/ica
Citation
Inorganica Chimica Acta, 2004, v. 357, p. 4389-4395 How to Cite?
AbstractChiral N,O pyridine alcohols HL1–HL6 were used to form complexes with copper(II) ions. Ligands HL1 and HL2 formed complexes with copper(II) ions when Cu(OAc)2 and HL were refluxed in methanol/ethanol mixture. Ligand HL3 formed a complex with copper(II) when deprotonated with NaH and stirred in a Cu(II) acetate THF solution. Ligands HL4–HL6 did not form complexes with copper(II) under similar conditions. Two complexes, [Cu(L1)2] and [Cu(L2)2], were isolated as single crystals and characterized by X-ray crystallography. These complexes showed low catalytic activities in asymmetric reactions. However, they became active when reacted with triflic acid. Copper complexes, [Cu(L)] or [Cu(L)]+, formed in situ by reacting ligands HL with copper(I) or (II) ions, respectively, were also found to be active copper catalysts for asymmetric cyclopropanation of styrene with ethyl diazoacetate and allylic oxidation of cyclohexene with t-butylperoxybenzoate. Enantioselectivities up to 56% and 38% were obtained in asymmetric cyclopropanation of styrene and asymmetric allylic oxidation of cyclohexene, respectively.
Persistent Identifierhttp://hdl.handle.net/10722/68955
ISSN
2015 Impact Factor: 1.918
2015 SCImago Journal Rankings: 0.584
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLee, WSen_HK
dc.contributor.authorLeung, HKen_HK
dc.contributor.authorCheng, LSen_HK
dc.contributor.authorNg, LYen_HK
dc.contributor.authorLee, CSen_HK
dc.contributor.authorHuang, KHen_HK
dc.contributor.authorWong, WTen_HK
dc.contributor.authorKwong, HLen_HK
dc.date.accessioned2010-09-06T06:09:14Z-
dc.date.available2010-09-06T06:09:14Z-
dc.date.issued2004en_HK
dc.identifier.citationInorganica Chimica Acta, 2004, v. 357, p. 4389-4395en_HK
dc.identifier.issn0020-1693en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68955-
dc.description.abstractChiral N,O pyridine alcohols HL1–HL6 were used to form complexes with copper(II) ions. Ligands HL1 and HL2 formed complexes with copper(II) ions when Cu(OAc)2 and HL were refluxed in methanol/ethanol mixture. Ligand HL3 formed a complex with copper(II) when deprotonated with NaH and stirred in a Cu(II) acetate THF solution. Ligands HL4–HL6 did not form complexes with copper(II) under similar conditions. Two complexes, [Cu(L1)2] and [Cu(L2)2], were isolated as single crystals and characterized by X-ray crystallography. These complexes showed low catalytic activities in asymmetric reactions. However, they became active when reacted with triflic acid. Copper complexes, [Cu(L)] or [Cu(L)]+, formed in situ by reacting ligands HL with copper(I) or (II) ions, respectively, were also found to be active copper catalysts for asymmetric cyclopropanation of styrene with ethyl diazoacetate and allylic oxidation of cyclohexene with t-butylperoxybenzoate. Enantioselectivities up to 56% and 38% were obtained in asymmetric cyclopropanation of styrene and asymmetric allylic oxidation of cyclohexene, respectively.-
dc.languageengen_HK
dc.publisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/icaen_HK
dc.relation.ispartofInorganica Chimica Actaen_HK
dc.subjectCatalyst-
dc.subjectChirality-
dc.subjectCrystal structure-
dc.subjectCyclopropanation-
dc.subjectEnantioselectivity-
dc.titleChiral 2-pyridyl alcoholate copper complexes: crystal structures of [bis(2-pyridyl alcoholate)copper(II)] and the use of [(2-pyridyl alcoholate)copper(II)]+ and [(2-pyridyl alcoholate)copper(I)] in asymmetric cyclopropanation of styrene and allylic oxen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0020-1693&volume=357&spage=4389&epage=4395&date=2004&atitle=Chiral+2-pyridyl+alcoholate+copper+complexes:+crystal+structures+of+[bis(2-pyridyl+alcoholate)copper(II)]+and+the+use+of+[(2-pyridyl+alcoholate)copper(II)]++and+[(2-pyridyl+alcoholate)copper(I)]+in+asymmetric+cyclopropanation+of+styrene+and+allylic+oxen_HK
dc.identifier.emailWong, WT: wtwong@hku.hken_HK
dc.identifier.authorityWong, WT=rp00811en_HK
dc.identifier.doi10.1016/j.ica.2004.06.043-
dc.identifier.scopuseid_2-s2.0-9244228500-
dc.identifier.hkuros100875en_HK
dc.identifier.volume357-
dc.identifier.spage4389-
dc.identifier.epage4395-
dc.identifier.isiWOS:000225612500005-
dc.publisher.placeNetherlands-

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