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Indium‐Catalyzed Synthesis of Keto Esters from Cyclic 1,3‐Diketones and Alcohols and Application to the Synthesis of Seratrodast
Author(s) -
Kuninobu Yoichiro,
Kawata Atsushi,
Noborio Taihei,
Yamamoto Syunichi,
Matsuki Takashi,
Takata Kazumi,
Takai Kazuhiko
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900553
Subject(s) - trifluoromethanesulfonate , chemistry , catalysis , regioselectivity , indium , organic chemistry , aldol reaction , medicinal chemistry , lewis acids and bases
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.