N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

Handle URI:
http://hdl.handle.net/10754/582931
Title:
N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides
Authors:
Guo, Hao; Xing, Fen; Du, Guang-Fen; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Dai, Bin; He, Lin
Abstract:
An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC)
Citation:
N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides 2015 The Journal of Organic Chemistry
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Organic Chemistry
Issue Date:
16-Nov-2015
DOI:
10.1021/acs.joc.5b01845
Type:
Article
ISSN:
0022-3263; 1520-6904
Is Supplemented By:
Guo, H., Xing, F., Du, G.-F., Huang, K.-W., Dai, B., & He, L. (2016). CCDC 1433704: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1k3wj2; DOI:10.5517/cc1k3wj2; HANDLE:http://hdl.handle.net/10754/624479
Additional Links:
http://pubs.acs.org/doi/10.1021/acs.joc.5b01845
Appears in Collections:
Articles; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorGuo, Haoen
dc.contributor.authorXing, Fenen
dc.contributor.authorDu, Guang-Fenen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorDai, Binen
dc.contributor.authorHe, Linen
dc.date.accessioned2015-11-30T13:13:45Zen
dc.date.available2015-11-30T13:13:45Zen
dc.date.issued2015-11-16en
dc.identifier.citationN-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides 2015 The Journal of Organic Chemistryen
dc.identifier.issn0022-3263en
dc.identifier.issn1520-6904en
dc.identifier.doi10.1021/acs.joc.5b01845en
dc.identifier.urihttp://hdl.handle.net/10754/582931en
dc.description.abstractAn efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.en
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/10.1021/acs.joc.5b01845en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/10.1021/acs.joc.5b01845.en
dc.titleN-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolidesen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalThe Journal of Organic Chemistryen
dc.eprint.versionPost-printen
dc.contributor.institutionSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region 832000, People’s Republic of Chinaen
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)en
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByGuo, H., Xing, F., Du, G.-F., Huang, K.-W., Dai, B., & He, L. (2016). CCDC 1433704: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1k3wj2en
dc.relation.isSupplementedByDOI:10.5517/cc1k3wj2en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624479en
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