N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides
Type
ArticleKAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2015-11-30Online Publication Date
2015-11-30Print Publication Date
2015-12-18Permanent link to this record
http://hdl.handle.net/10754/582931
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Show full item recordAbstract
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.Citation
N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides 2015 The Journal of Organic ChemistryPublisher
American Chemical Society (ACS)Journal
The Journal of Organic ChemistryPubMed ID
26569552Additional Links
http://pubs.acs.org/doi/10.1021/acs.joc.5b01845Relations
Is Supplemented By:- [Dataset]
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: 10754/624479
ae974a485f413a2113503eed53cd6c53
10.1021/acs.joc.5b01845
Scopus Count
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