jo8b01294_si_004.cif (1.25 MB)
Harnessing Nucleophilicity of Allenol Ester with p-Quinone Methides via Gold Catalysis: Application to the Synthesis of Diarylmethine-Substituted Enones
dataset
posted on 2018-06-20, 00:00 authored by Brijesh
M. Sharma, Jayant Rathod, Rajesh G. Gonnade, Pradeep KumarA 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.
History
Usage metrics
Categories
Keywords
Lewis acidselectivityfunctionalized diarylmethine-substituted enonesApplicationQuinone Methidesgold catalystconjugateAllenol Esternucleophilic attackπ- acid-triggered activationsubstrate scopesigmatropicMorita-Baylis-HillmanNucleophilicityGold Catalysisaccessnucleophilic allenol esterroleSynthesiyieldrearrangementquinone methidesMBHmethodalkyneDiarylmethine-Substituted EnonesQM
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC