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Article: Synthesis of cyclohexenols and cycloheptenols via the regioselective reductive ring opening of oxabicyclic compounds

TitleSynthesis of cyclohexenols and cycloheptenols via the regioselective reductive ring opening of oxabicyclic compounds
Authors
Issue Date1997
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, 1997, v. 119 n. 28, p. 6478-6487 How to Cite?
AbstractThe reductive ring opening of oxabicyclic compounds has been achieved. While RMgBr/MgBr2 works in a few limited substrates, diisobutylaluminum hydride reacts with oxabicyclic[3.2.1]- and -[2.2.1]alkenes to provide cycloheptenols and cyclohexenols in good yield and in some cases in good regioselectivity. With some substrates further reduction of the alkene was observed which led us to examine transition metals such as nickel which are known to accelerate the hydroalumination reaction. The reaction with Ni(COD)2 (COD = cyclooctadiene) gave the best reactivity-selectivity profile, and significantly higher yields were obtained with minimal overreduction of the alkene. Phosphine ligands were shown to dramatically improve the regioselectivity of ring opening of bridgehead-substituted oxabicyclic compounds. The best ligand was 1,4-bis(diphenylphosphino)butane which gave up to 380:1 selectivity. A series of deuterium quenching experiments showed that the selectivity of the hydroalumination varies according to the reaction protocol and ligand-metal ratio.
Persistent Identifierhttp://hdl.handle.net/10722/167562
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLautens, Men_US
dc.contributor.authorMa, Sen_US
dc.contributor.authorChiu, Pen_US
dc.date.accessioned2012-10-08T03:08:31Z-
dc.date.available2012-10-08T03:08:31Z-
dc.date.issued1997en_US
dc.identifier.citationJournal Of The American Chemical Society, 1997, v. 119 n. 28, p. 6478-6487en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/167562-
dc.description.abstractThe reductive ring opening of oxabicyclic compounds has been achieved. While RMgBr/MgBr2 works in a few limited substrates, diisobutylaluminum hydride reacts with oxabicyclic[3.2.1]- and -[2.2.1]alkenes to provide cycloheptenols and cyclohexenols in good yield and in some cases in good regioselectivity. With some substrates further reduction of the alkene was observed which led us to examine transition metals such as nickel which are known to accelerate the hydroalumination reaction. The reaction with Ni(COD)2 (COD = cyclooctadiene) gave the best reactivity-selectivity profile, and significantly higher yields were obtained with minimal overreduction of the alkene. Phosphine ligands were shown to dramatically improve the regioselectivity of ring opening of bridgehead-substituted oxabicyclic compounds. The best ligand was 1,4-bis(diphenylphosphino)butane which gave up to 380:1 selectivity. A series of deuterium quenching experiments showed that the selectivity of the hydroalumination varies according to the reaction protocol and ligand-metal ratio.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_US
dc.relation.ispartofJournal of the American Chemical Societyen_US
dc.titleSynthesis of cyclohexenols and cycloheptenols via the regioselective reductive ring opening of oxabicyclic compoundsen_US
dc.typeArticleen_US
dc.identifier.emailChiu, P:pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ja964361jen_US
dc.identifier.scopuseid_2-s2.0-0030810474en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0030810474&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume119en_US
dc.identifier.issue28en_US
dc.identifier.spage6478en_US
dc.identifier.epage6487en_US
dc.identifier.isiWOS:A1997XL34300004-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLautens, M=26643350000en_US
dc.identifier.scopusauthoridMa, S=7403725552en_US
dc.identifier.scopusauthoridChiu, P=11140148700en_US

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