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Article: Kinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones

TitleKinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones
Authors
Issue Date2001
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2001, v. 66 n. 13, p. 4619-4624 How to Cite?
AbstractKinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl 3, tert-butyl, or CF 3 group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.
Persistent Identifierhttp://hdl.handle.net/10722/70465
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorJiao, GSen_HK
dc.contributor.authorYip, YCen_HK
dc.contributor.authorLai, THen_HK
dc.contributor.authorWong, MKen_HK
dc.date.accessioned2010-09-06T06:23:08Z-
dc.date.available2010-09-06T06:23:08Z-
dc.date.issued2001en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2001, v. 66 n. 13, p. 4619-4624en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70465-
dc.description.abstractKinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl 3, tert-butyl, or CF 3 group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.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.titleKinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketonesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=66&spage=4619&epage=4624&date=2001&atitle=Kinetic+Resolution+of+Acyclic+Secondary+Allylic+Silyl+Ethers+Catalyzed+by+chiral+Ketonesen_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/jo010068cen_HK
dc.identifier.pmid11421782-
dc.identifier.scopuseid_2-s2.0-0035967763en_HK
dc.identifier.hkuros58727en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035967763&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume66en_HK
dc.identifier.issue13en_HK
dc.identifier.spage4619en_HK
dc.identifier.epage4624en_HK
dc.identifier.isiWOS:000169536700020-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridJiao, GS=36777307800en_HK
dc.identifier.scopusauthoridYip, YC=7005596386en_HK
dc.identifier.scopusauthoridLai, TH=37161683300en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK

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