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Article: Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

TitleGold-catalyzed highly enantioselective synthesis of axially chiral allenes
Authors
Lo, VKYWong, MKChe, CM
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2008, v. 10 n. 3, p. 517-519 How to Cite?
DOI: http://dx.doi.org/10.1021/ol702970r
AbstractAxially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4 in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/129115
ISSN
1523-7060
2023 Impact Factor: 4.9
2023 SCImago Journal Rankings: 1.245
ISI Accession Number ID
WOS:000252648200040
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorLo, VKYen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-12-23T08:32:43Z-
dc.date.available2010-12-23T08:32:43Z-
dc.date.issued2008en_HK
dc.identifier.citationOrganic Letters, 2008, v. 10 n. 3, p. 517-519en_HK
dc.identifier.issn1523-7060en_HK
dc.identifier.urihttp://hdl.handle.net/10722/129115-
dc.description.abstractAxially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4 in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture. © 2008 American Chemical Society.en_HK
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_HK
dc.relation.ispartofOrganic Lettersen_HK
dc.titleGold-catalyzed highly enantioselective synthesis of axially chiral allenesen_HK
dc.typeArticleen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ol702970ren_HK
dc.identifier.pmid18181641-
dc.identifier.scopuseid_2-s2.0-38949112395en_HK
dc.identifier.hkuros177354en_US
dc.identifier.hkuros147488-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-38949112395&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume10en_HK
dc.identifier.issue3en_HK
dc.identifier.spage517en_HK
dc.identifier.epage519en_HK
dc.identifier.isiWOS:000252648200040-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLo, VKY=13406071200en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.issnl1523-7052-

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