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

Hao Guo, Fen Xing, Guang-Fen Du, Kuo-Wei Huang, Bin Dai, Lin He

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)12606-12613
Number of pages8
JournalThe Journal of Organic Chemistry
Volume80
Issue number24
DOIs
StatePublished - Nov 30 2015

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