Harnessing Nucleophilicity of Allenol Ester with p-Quinone Methides via Gold Catalysis: Application to the Synthesis of Diarylmethine-Substituted Enones
datasetposted on 20.06.2018, 00:00 by Brijesh M. Sharma, Jayant Rathod, Rajesh G. Gonnade, Pradeep Kumar
A gold(I)-catalyzed protocol for intermolecular 1,6-conjugate addition of nucleophilic allenol ester generated in situ through [3,3]-sigmatropic rearrangement with p-quinone methides (p-QMs) has been developed. The gold catalyst plays a dual role by the π-acid-triggered activation of alkynes and at the same time as a Lewis acid for activation of p-QMs toward nucleophilic attack. This method enables rapid access to a wide range of densely functionalized diarylmethine-substituted enones, a Morita-Baylis-Hillman (MBH) product with high selectivity, excellent yields, and broad substrate scope.
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Lewis acidselectivityfunctionalized diarylmethine-substituted enonesApplicationQuinone Methidesgold catalystconjugateAllenol Esternucleophilic attackπ- acid-triggered activationsubstrate scopesigmatropicMorita-Baylis-HillmanNucleophilicityGold Catalysisaccessnucleophilic allenol esterroleSynthesiyieldrearrangementquinone methidesMBHmethodalkyneDiarylmethine-Substituted EnonesQM