N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Permanent link to this recordhttp://hdl.handle.net/10754/582931
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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.
CitationN-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides 2015 The Journal of Organic Chemistry
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry
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