1433174-92-5Relevant articles and documents
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.