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Article: Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone

TitleFluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone
Authors
Issue Date2005
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2005, v. 70 n. 3, p. 898-906 How to Cite?
Abstract(Chemical Equation Presented) We have synthesized a series of chiral cyclic secondary amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine plays a dual role - as a phase transfer catalyst and an Oxone activator - in these epoxidation reactions. The slightly acidic reaction conditions we employed in this work obviate the need to preform ammonium salts, which are the actual catalysts that mediate the epoxidations.
Persistent Identifierhttp://hdl.handle.net/10722/70491
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorHo, CYen_HK
dc.contributor.authorChen, YCen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorYang, Den_HK
dc.date.accessioned2010-09-06T06:23:22Z-
dc.date.available2010-09-06T06:23:22Z-
dc.date.issued2005en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2005, v. 70 n. 3, p. 898-906en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70491-
dc.description.abstract(Chemical Equation Presented) We have synthesized a series of chiral cyclic secondary amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine plays a dual role - as a phase transfer catalyst and an Oxone activator - in these epoxidation reactions. The slightly acidic reaction conditions we employed in this work obviate the need to preform ammonium salts, which are the actual catalysts that mediate the epoxidations.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleFluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxoneen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=70&spage=898&epage=906&date=2005&atitle=Fluorinated+chiral+secondary+amines+as+catalysts+for+epoxidation+of+olefins+with+oxoneen_HK
dc.identifier.emailYang, D:yangdan@hku.hken_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo048378ten_HK
dc.identifier.scopuseid_2-s2.0-13244292377en_HK
dc.identifier.hkuros119233en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-13244292377&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume70en_HK
dc.identifier.issue3en_HK
dc.identifier.spage898en_HK
dc.identifier.epage906en_HK
dc.identifier.isiWOS:000226777100018-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridHo, CY=35310593500en_HK
dc.identifier.scopusauthoridChen, YC=35242054800en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK

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