149379-91-9Relevant academic research and scientific papers
Controlling the α/γ-Reactivity of Vinylogous Ketone Enolates in Organocatalytic Enantioselective Michael Reactions
Iriarte, Igor,Olaizola, Olatz,Vera, Silvia,Gamboa, I?aki,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 8860 - 8864 (2017/07/17)
The first regio-, diastereo-, and enantioselective direct Michael reaction of β,γ-unsaturated ketones with nitroolefins is enabled by Br?nsted base/hydrogen-bonding bifunctional catalysis. A squaramide-substituted tertiary amine catalyzes the reaction of a broad range of β,γ-unsaturated ketones to proceed at the α-site exclusively, giving rise to adducts with two consecutive tertiary carbon stereocenters in diastereomeric ratios of up to >20:1 and enantioselectivities generally in the 90–98 % ee range.
Transition-metal-free superbase-promoted stereoselective α-vinylation of ketones with arylacetylenes: A general strategy for synthesis of β,γ-unsaturated ketones
Trofimov, Boris A.,Schmidt, Elena Yu.,Zorina, Nadezhda V.,Ivanova, Elena V.,Ushakov, Igor A.
experimental part, p. 6880 - 6886 (2012/09/22)
A wide variety of β,γ-unsaturated ketones of E configuration have been obtained in good to excellent yields via KOtBu/DMSO promoted α-vinylation of aliphatic, cycloaliphatic, and alkyl aromatic (heteroaromatic) ketones with diverse arylacetylenes.
