73968-80-6Relevant academic research and scientific papers
Reactivity of a-trifluoromethanesulfonyl esters, amides and ketones: Decarboxylative allylation, methylation, and enol formation
Kong, Han Il,Gill, Monica A.,Hrdina, Amy H.,Crichton, Jennifer E.,Manthorpe, Jeffrey M.
supporting information, p. 151 - 161 (2013/11/06)
The impact of α-trifluoromethanesulfonyl groups on the chemistry of various carbonyl groups is reported. Allylic α, α-dialkylated- α-trifluoromethanesulfonyl esters readily underwent decarboxylative allylation. α-Trifluoromethylsulfonyl esters, ketones, and amides were all methylated in the presence of trimethylsilyldiazomethane. Esters afforded a mixture of O-and C-methylation; however, ketones and amides offered exclusively O-methylation, with varying degrees of E/Z selectivity, thus affording ambiphilic alkenes. α-Trifluoromethanesulfonyl ketones also exhibited keto-enol tautomerism.
Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane
Kong, Han Il,Crichton, Jennifer E.,Manthorpe, Jeffrey M.
supporting information; experimental part, p. 3714 - 3717 (2011/08/06)
α-Trifluoromethanesulfonyl esters, ketones and amides are C-H acids capable of reacting with trimethylsilyldiazomethane to afford the corresponding ambiphilic alkenes. While esters were found to be non-selective, ketones were highly regioselective for O-methylation and displayed variable E/Z stereoselectivity. Amides were observed to be both highly regio- and stereoselective, affording O-methylation with exclusive formation of the Z-alkene.
