TY - JOUR
T1 - Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
AU - Kuninobu, Yoichiro
AU - Kawata, Atsushi
AU - Noborio, Taihei
AU - Yamamoto, Syun Ichi
AU - Matsuki, Takashi
AU - Takata, Kazumi
AU - Takai, Kazuhiko
PY - 2010/4/1
Y1 - 2010/4/1
N2 - 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.
AB - 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.
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U2 - 10.1002/asia.200900553
DO - 10.1002/asia.200900553
M3 - Article
C2 - 20235270
AN - SCOPUS:77950846274
SN - 1861-4728
VL - 5
SP - 941
EP - 945
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 4
ER -