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Article: Phosphonium ion tagged chiral phosphoric acids and their application in Friedel-Crafts reactions of indoles

TitlePhosphonium ion tagged chiral phosphoric acids and their application in Friedel-Crafts reactions of indoles
Authors
KeywordsAsymmetric catalysis
Chiral phosphoric acid
Friedel-Crafts reactions
Organocatalysis
Phosphonium salt
Issue Date2011
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2011, v. 67 n. 22, p. 4103-4109 How to Cite?
AbstractThe attachment of phosphonium ion phase tags to chiral binapthyl-based phosphoric acid catalysts, and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles has been studied. Placement of the tags at the 3 and 3′ positions of the phosphoric acid, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6′ positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily removed at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. © 2011 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/139014
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
Funding AgencyGrant Number
University of Hong Kong
Research Grants Council of the Hong Kong SAR, PR of ChinaHKU 705209P
Funding Information:

This research was supported financially by the University of Hong Kong and the Research Grants Council of the Hong Kong SAR, PR of China (Project No. HKU 705209P), and Mr. Jun Ou performed some preliminary experiments.

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorHermeke, Jen_HK
dc.contributor.authorToy, PHen_HK
dc.date.accessioned2011-09-23T05:44:05Z-
dc.date.available2011-09-23T05:44:05Z-
dc.date.issued2011en_HK
dc.identifier.citationTetrahedron, 2011, v. 67 n. 22, p. 4103-4109en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/139014-
dc.description.abstractThe attachment of phosphonium ion phase tags to chiral binapthyl-based phosphoric acid catalysts, and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles has been studied. Placement of the tags at the 3 and 3′ positions of the phosphoric acid, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6′ positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily removed at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. © 2011 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.subjectAsymmetric catalysisen_HK
dc.subjectChiral phosphoric aciden_HK
dc.subjectFriedel-Crafts reactionsen_HK
dc.subjectOrganocatalysisen_HK
dc.subjectPhosphonium salten_HK
dc.titlePhosphonium ion tagged chiral phosphoric acids and their application in Friedel-Crafts reactions of indolesen_HK
dc.typeArticleen_HK
dc.identifier.emailToy, PH:phtoy@hkucc.hku.hken_HK
dc.identifier.authorityToy, PH=rp00791en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.tet.2011.03.105en_HK
dc.identifier.scopuseid_2-s2.0-79955872367en_HK
dc.identifier.hkuros195893en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79955872367&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume67en_HK
dc.identifier.issue22en_HK
dc.identifier.spage4103en_HK
dc.identifier.epage4109en_HK
dc.identifier.eissn1464-5416-
dc.identifier.isiWOS:000291140100019-
dc.publisher.placeUnited Kingdomen_HK
dc.relation.projectPolymer-Supported, Polymeric and Phase-Tagged Chiral Phosphoric Acids for Asymmetric Catalysis-
dc.identifier.scopusauthoridHermeke, J=37110916000en_HK
dc.identifier.scopusauthoridToy, PH=7006579247en_HK

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