Indium-catalyzed retro-claisen condensation

Atsushi Kawata, Kazumi Takata, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)7793-7795
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number41
DOIs
Publication statusPublished - 2007

Fingerprint

Indium
Condensation
Alcohols
Carbon
Nucleophiles
Carboxylic Acids
Carboxylic acids
Amides
Amines
Esters
Water

Keywords

  • C-C activation
  • Esters
  • Indium
  • Retro reactions
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Indium-catalyzed retro-claisen condensation. / Kawata, Atsushi; Takata, Kazumi; Kuninobu, Yoichiro; Takai, Kazuhiko.

In: Angewandte Chemie - International Edition, Vol. 46, No. 41, 2007, p. 7793-7795.

Research output: Contribution to journalArticle

Kawata, Atsushi ; Takata, Kazumi ; Kuninobu, Yoichiro ; Takai, Kazuhiko. / Indium-catalyzed retro-claisen condensation. In: Angewandte Chemie - International Edition. 2007 ; Vol. 46, No. 41. pp. 7793-7795.
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