104322-69-2Relevant academic research and scientific papers
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.
, p. 3809 - 3812 (2008)
(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.
