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Article: The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

TitleThe rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates
Authors
Shi, BMerten, SWong, DKYChu, JCKLiu, LLLam, SKJäger, AWong, WTChiu, PMetz, P
KeywordsAsymmetric reduction
Cycloaddition
Domino reactions
Sulfur heterocycles
Transition metal catalysis
Issue Date2009
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley.com/bw/journal.asp?ref=1615-4150
Citation
Advanced Synthesis And Catalysis, 2009, v. 351 n. 18, p. 3128-3132 How to Cite?
DOI: http://dx.doi.org/10.1002/adsc.200900695
AbstractVinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/69704
ISSN
1615-4150
2021 Impact Factor: 5.981
2020 SCImago Journal Rankings: 1.541
ISI Accession Number ID
WOS:000273394500017
Funding AgencyGrant Number
DFGME 776/15-2
DAADD/03/314304
G HK026/03
RGCHKU 7018/07P
AoE Scheme of UGC Hong KongAoE/P-10/01
Funding Information:

Financial support of this work by the DFG (ME 776/15-2), the DAAD (D/03/314304), DAAD-RGC (G HK026/03), RGC (HKU 7018/07P), and the AoE Scheme of UGC Hong Kong (AoE/P-10/01), is gratefully acknowledged.

References
References in Scopus
Grants
Institute of molecular technology for drug discovery and synthesis

 

DC FieldValueLanguage
dc.contributor.authorShi, Ben_HK
dc.contributor.authorMerten, Sen_HK
dc.contributor.authorWong, DKYen_HK
dc.contributor.authorChu, JCKen_HK
dc.contributor.authorLiu, LLen_HK
dc.contributor.authorLam, SKen_HK
dc.contributor.authorJäger, Aen_HK
dc.contributor.authorWong, WTen_HK
dc.contributor.authorChiu, Pen_HK
dc.contributor.authorMetz, Pen_HK
dc.date.accessioned2010-09-06T06:16:05Z-
dc.date.available2010-09-06T06:16:05Z-
dc.date.issued2009en_HK
dc.identifier.citationAdvanced Synthesis And Catalysis, 2009, v. 351 n. 18, p. 3128-3132en_HK
dc.identifier.issn1615-4150en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69704-
dc.description.abstractVinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley.com/bw/journal.asp?ref=1615-4150en_HK
dc.relation.ispartofAdvanced Synthesis and Catalysisen_HK
dc.subjectAsymmetric reductionen_HK
dc.subjectCycloadditionen_HK
dc.subjectDomino reactionsen_HK
dc.subjectSulfur heterocyclesen_HK
dc.subjectTransition metal catalysisen_HK
dc.titleThe rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonatesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1615-4150&volume=351&spage=3128&epage=3132&date=2009&atitle=The+Rhodium-Catalyzed+Carbene+Cyclization+Cycloaddition Cascade+Reaction+of+Vinylsulfonatesen_HK
dc.identifier.emailLam, SK: secant@hku.hken_HK
dc.identifier.emailWong, WT: wtwong@hku.hken_HK
dc.identifier.emailChiu, P: pchiu@hku.hken_HK
dc.identifier.authorityLam, SK=rp00720en_HK
dc.identifier.authorityWong, WT=rp00811en_HK
dc.identifier.authorityChiu, P=rp00680en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/adsc.200900695en_HK
dc.identifier.scopuseid_2-s2.0-73349090868en_HK
dc.identifier.hkuros170185en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-73349090868&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume351en_HK
dc.identifier.issue18en_HK
dc.identifier.spage3128en_HK
dc.identifier.epage3132en_HK
dc.identifier.eissn1615-4169-
dc.identifier.isiWOS:000273394500017-
dc.publisher.placeGermanyen_HK
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridShi, B=35270116500en_HK
dc.identifier.scopusauthoridMerten, S=23019098700en_HK
dc.identifier.scopusauthoridWong, DKY=35270312600en_HK
dc.identifier.scopusauthoridChu, JCK=35267922700en_HK
dc.identifier.scopusauthoridLiu, LL=35215540300en_HK
dc.identifier.scopusauthoridLam, SK=8560491900en_HK
dc.identifier.scopusauthoridJäger, A=14319076300en_HK
dc.identifier.scopusauthoridWong, WT=7403973084en_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK
dc.identifier.scopusauthoridMetz, P=7103110683en_HK
dc.identifier.issnl1615-4150-

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