83181-30-0Relevant academic research and scientific papers
InBr3-Catalyzed Coupling Reaction between Electron-Deficient Alkenyl Ethers with Silyl Enolates for Stereoselective Synthesis of 1,5-Dioxo-alk-2-enes
Nakao, Shuichi,Saikai, Miki,Nishimoto, Yoshihiro,Yasuda, Makoto
, p. 77 - 81 (2021)
A coupling reaction of electron-deficient alkenyl ethers with silyl enolates catalyzed by InBr3 was achieved. Various silyl enolates and 2-carbonylalkenyl ethers were applicable, giving the corresponding 1,5-dioxo-alk-2-enes with perfect stereoselectivity of the alkene moieties. The present coupling reaction proceeds via the 1,4-addition of silyl enolates to alkenyl ethers followed by elimination of silyl alkoxides, in which moderate-Lewis acidic InBr3 performs both the activation of alkenyl ethers and the elimination of alkoxy groups regardless of the presence of various coordinative functional groups.
O-SILYLATED ENOLATE PHENYLTHIOALKYLATION: A NEW SYNTHESIS OF UNSATURATED 1,5-DICARBONYL COMPOUNDS.
Khan, Hassan A.,Paterson, Ian
, p. 2399 - 2402 (2007/10/02)
The O-silylated enolates of ketones and esters can be phenylthioalkylated by the chlorides (2) and (3) under ZnBr2-catalysis; ozonolysis and subsequent sulphoxide thermolysis then gives the corresponding unsaturated 1,5-dicarbonyl compounds.
