- Retro-claisen condensation with FeIII as catalyst under solvent-free conditions
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An iron(III) salt catalyzed retro-Claisen condensation between an alcohol and a 1,3-diketone was investigated. The mechanism involves the formation of a metal-induced sixmembered cyclic transition state and cleavage of the C sp2-Csp3 bond. Regioselective esterification and one-pot couversion of silyl ethers into esters with good yields was observed. Simple reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method.
- Rao, Chitturi Bhujanga,Rao, Dasireddi Chandra,Babu, Dokuburra Chanti,Venkateswarlu, Yenamandra
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supporting information; experimental part
p. 2855 - 2859
(2010/08/05)
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- Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
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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.
- Kuninobu, Yoichiro,Kawata, Atsushi,Noborio, Taihei,Yamamoto, Syun-Ichi,Matsuki, Takashi,Takata, Kazumi,Takai, Kazuhiko
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experimental part
p. 941 - 945
(2010/07/07)
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