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Article: Facial selectivity and stereospecificity in the (4 + 3) cycloaddition of epoxy enol silanes

TitleFacial selectivity and stereospecificity in the (4 + 3) cycloaddition of epoxy enol silanes
Authors
Lo, BChiu, P
Issue Date2011
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2011, v. 13 n. 5, p. 864-867 How to Cite?
DOI: http://dx.doi.org/10.1021/ol102897d
AbstractThe scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.(Figure Presented) © 2011 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/135346
ISSN
1523-7060
2021 Impact Factor: 6.072
2020 SCImago Journal Rankings: 1.940
ISI Accession Number ID
WOS:000287645800011
Funding AgencyGrant Number
University of Hong Kong Strategic Research Theme on Drugs
Council of Hong Kong SARGRF HKU 7017/06P
7015/10P
Funding Information:

This work was supported by the University of Hong Kong Strategic Research Theme on Drugs, and by the Research Grants Council of Hong Kong SAR (GRF HKU 7017/06P, 7015/10P). B.L. thanks the HKU Department of Chemistry for conference support.

References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorLo, Ben_HK
dc.contributor.authorChiu, Pen_HK
dc.date.accessioned2011-07-27T01:33:56Z-
dc.date.available2011-07-27T01:33:56Z-
dc.date.issued2011en_HK
dc.identifier.citationOrganic Letters, 2011, v. 13 n. 5, p. 864-867en_HK
dc.identifier.issn1523-7060en_HK
dc.identifier.urihttp://hdl.handle.net/10722/135346-
dc.description.abstractThe scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.(Figure Presented) © 2011 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.subject.meshAlkenes - chemistry-
dc.subject.meshCatalysis-
dc.subject.meshEpoxy Compounds - chemistry-
dc.subject.meshSilanes - chemistry-
dc.subject.meshStereoisomerism-
dc.titleFacial selectivity and stereospecificity in the (4 + 3) cycloaddition of epoxy enol silanesen_HK
dc.typeArticleen_HK
dc.identifier.emailChiu, P:pchiu@hku.hken_HK
dc.identifier.authorityChiu, P=rp00680en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ol102897den_HK
dc.identifier.pmid21275427-
dc.identifier.scopuseid_2-s2.0-79952119239en_HK
dc.identifier.hkuros186261en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79952119239&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume13en_HK
dc.identifier.issue5en_HK
dc.identifier.spage864en_HK
dc.identifier.epage867en_HK
dc.identifier.isiWOS:000287645800011-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLo, B=29767616700en_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK
dc.identifier.issnl1523-7052-

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