1052108-49-2Relevant academic research and scientific papers
A practical synthesis of b-keto thioesters by direct crossed-claisen coupling of thioesters and N-acylbenzotriazoles
Zhou, Guoqiang,Lim, Daniel,Fang, Fang,Coltart, Don M.
experimental part, p. 3350 - 3352 (2010/03/03)
Thioesters undergo chemoselective soft enolization and acylation with N-acylbenzotriazoles on treatment with MgBr2?OEt2 and i-Pr2NEt to give b-keto thioesters. Prior enolate formation is not required and the reaction is conducted using untreated dichlorom
Direct carbon - Carbon bond formation via chemoselective soft enolization of thioesters: A remarkably simple and versatile crossed-claisen reaction applied to the synthesis of LY294002
Zhou, Guoqiang,Lim, Daniel,Coltart, Don M.
supporting information; experimental part, p. 3809 - 3812 (2009/07/01)
(Chemical Equation Presented) Thioesters undergo chemoselective soft enolization and acylation by N-acylbenzotriazoles on treatment with MgBr 2·OEt2 and i-Pr2NEt to give β-keto thloesters. Prior enolate formation is not required, and the reaction is conducted using untreated CH2Cl2 open to the air. The coupled products are stable synthetic equivalents of β-keto acids and can be converted directly into β-keto esters, β-keto amides, and β-diketones under mild conditions. The utility of this carbon-carbon bond-forming method is shown through the synthesis of the PI3-K inhibitor LY294002.
