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Article: Influence of Michael acceptor stereochemistry on intramolecular Morita-Baylis-Hillman reactions

TitleInfluence of Michael acceptor stereochemistry on intramolecular Morita-Baylis-Hillman reactions
Authors
Issue Date2006
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2006, v. 71 n. 1, p. 368-371 How to Cite?
AbstractA study of the effect of Michael acceptor stereochemistry on the efficiency of intramolecular Morita-Baylis-Hillman (MBH) reactions has been performed. The reactions were catalyzed by a phosphine, and the reaction substrates studied were enones containing a pendant aldehyde moiety attached at the β-position of the alkene group. In all cases examined with PPh 3 as the catalyst, cyclization substrates possessing (Z)-alkene stereochemistry afforded a much higher yield of the desired product than did the E isomeric substrates under identical reaction conditions. This was also true when a polymer-supported phosphine catalyst was used. While both alkene isomers afforded the same product, in parallel reactions, the Z isomer afforded 2.5-8.5 times higher yield than did the corresponding E isomer. It is proposed that steric effects are a possible source of this dramatic difference in reactivity. Substrates where the β-substituent is cis to the electron-withdrawing substituent are relatively more accessible to react with the nucleophile catalyst than are their trans counterparts. These findings are expected to be useful in the design of synthetic intermediates, as intramolecular MBH reactions are being increasingly used in the preparation of complex synthetic targets. © 2006 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/69866
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorTeng, WDen_HK
dc.contributor.authorHuang, Ren_HK
dc.contributor.authorKwong, CKWen_HK
dc.contributor.authorShi, Men_HK
dc.contributor.authorToy, PHen_HK
dc.date.accessioned2010-09-06T06:17:33Z-
dc.date.available2010-09-06T06:17:33Z-
dc.date.issued2006en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2006, v. 71 n. 1, p. 368-371en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69866-
dc.description.abstractA study of the effect of Michael acceptor stereochemistry on the efficiency of intramolecular Morita-Baylis-Hillman (MBH) reactions has been performed. The reactions were catalyzed by a phosphine, and the reaction substrates studied were enones containing a pendant aldehyde moiety attached at the β-position of the alkene group. In all cases examined with PPh 3 as the catalyst, cyclization substrates possessing (Z)-alkene stereochemistry afforded a much higher yield of the desired product than did the E isomeric substrates under identical reaction conditions. This was also true when a polymer-supported phosphine catalyst was used. While both alkene isomers afforded the same product, in parallel reactions, the Z isomer afforded 2.5-8.5 times higher yield than did the corresponding E isomer. It is proposed that steric effects are a possible source of this dramatic difference in reactivity. Substrates where the β-substituent is cis to the electron-withdrawing substituent are relatively more accessible to react with the nucleophile catalyst than are their trans counterparts. These findings are expected to be useful in the design of synthetic intermediates, as intramolecular MBH reactions are being increasingly used in the preparation of complex synthetic targets. © 2006 American Chemical Society.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.titleInfluence of Michael acceptor stereochemistry on intramolecular Morita-Baylis-Hillman reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=71&spage=368&epage=371&date=2006&atitle=Influence+of+michael+acceptor+stereochemistry+on+intramolecular+morita-baylis-hillman+reactionsen_HK
dc.identifier.emailToy, PH:phtoy@hkucc.hku.hken_HK
dc.identifier.authorityToy, PH=rp00791en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo051802len_HK
dc.identifier.scopuseid_2-s2.0-31144439127en_HK
dc.identifier.hkuros117922en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-31144439127&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume71en_HK
dc.identifier.issue1en_HK
dc.identifier.spage368en_HK
dc.identifier.epage371en_HK
dc.identifier.isiWOS:000234438700052-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridTeng, WD=9634844800en_HK
dc.identifier.scopusauthoridHuang, R=55216156500en_HK
dc.identifier.scopusauthoridKwong, CKW=13306659700en_HK
dc.identifier.scopusauthoridShi, M=7201370444en_HK
dc.identifier.scopusauthoridToy, PH=7006579247en_HK

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