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Article: Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

TitleDesign and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins
Authors
Issue Date1998
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 1998, v. 120 n. 24, p. 5943-5952 How to Cite?
AbstractA series of C2 symmetric chiral ketones were designed and synthesized for catalytic asymmetric epoxidation of unfunctionalized olefins. Among those ketones screened, (R)-7, (R)-9, and (R)-10 were found to be highly efficient catalysts for epoxidation of trans-stilbenes with enantioselectivities in the range of 84-95%. Convincing evidence was provided for a spiro transition state of dioxirane epoxidation. Through the 18O-labeling experiment, chiral dioxiranes were found to be the intermediates in chiral ketone catalyzed epoxidation reactions.
Persistent Identifierhttp://hdl.handle.net/10722/69661
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.date.accessioned2010-09-06T06:15:42Z-
dc.date.available2010-09-06T06:15:42Z-
dc.date.issued1998en_HK
dc.identifier.citationJournal Of The American Chemical Society, 1998, v. 120 n. 24, p. 5943-5952en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69661-
dc.description.abstractA series of C2 symmetric chiral ketones were designed and synthesized for catalytic asymmetric epoxidation of unfunctionalized olefins. Among those ketones screened, (R)-7, (R)-9, and (R)-10 were found to be highly efficient catalysts for epoxidation of trans-stilbenes with enantioselectivities in the range of 84-95%. Convincing evidence was provided for a spiro transition state of dioxirane epoxidation. Through the 18O-labeling experiment, chiral dioxiranes were found to be the intermediates in chiral ketone catalyzed epoxidation reactions.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_HK
dc.relation.ispartofJournal of the American Chemical Societyen_HK
dc.titleDesign and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefinsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=120&issue=24&spage=5943&epage=5952&date=1998&atitle=Design+and+synthesis+of+chiral+ketones+for+catalytic+asymmetric+epoxidation+of+unfunctionalized+olefinsen_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/ja980428men_HK
dc.identifier.scopuseid_2-s2.0-0031749334en_HK
dc.identifier.hkuros32404en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0031749334&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume120en_HK
dc.identifier.issue24en_HK
dc.identifier.spage5943en_HK
dc.identifier.epage5952en_HK
dc.identifier.isiWOS:000074419100010-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK

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