960305-75-3Relevant academic research and scientific papers
Indium-catalyzed retro-claisen condensation
Kawata, Atsushi,Takata, Kazumi,Kuninobu, Yoichiro,Takai, Kazuhiko
, p. 7793 - 7795 (2007)
(Chemical Equation Presented) Retro-aldol reaction: Indium-catalyzed reaction of a 1,3-diketone with an alcohol proceeds under solvent-free conditions by nucleophilic attack of the alcohol on a carbonyl group of the 1,3-diketone and carbon-carbon bond cleavage by a retro-Claisen condensation to give an ester in high yield (see scheme). Using water and an amine as nucleophiles instead of an alcohol gave the corresponding carboxylic acid and amide.
Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
Kuninobu, Yoichiro,Kawata, Atsushi,Noborio, Taihei,Yamamoto, Syun-Ichi,Matsuki, Takashi,Takata, Kazumi,Takai, Kazuhiko
experimental part, p. 941 - 945 (2010/07/07)
Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.
