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Indium‐Catalyzed Retro‐Claisen Condensation
Author(s) -
Kawata Atsushi,
Takata Kazumi,
Kuninobu Yoichiro,
Takai Kazuhiko
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702798
Subject(s) - nucleophile , chemistry , claisen condensation , indium , aldol condensation , alcohol , amide , amine gas treating , yield (engineering) , claisen rearrangement , catalysis , organic chemistry , medicinal chemistry , materials science , metallurgy
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.