Indium-catalyzed retro-claisen condensation

Atsushi Kawata; Kazumi Takata; Yoichiro Kuninobu; Kazuhiko Takai

doi:10.1002/anie.200702798

Indium-catalyzed retro-claisen condensation

Atsushi Kawata, Kazumi Takata, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

107 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 language	English
Pages (from-to)	7793-7795
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	41
DOIs	https://doi.org/10.1002/anie.200702798
Publication status	Published - Oct 26 2007

Keywords

C-C activation
Esters
Indium
Retro reactions
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200702798

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AU - Kawata, Atsushi

AU - Takata, Kazumi

AU - Kuninobu, Yoichiro

AU - Takai, Kazuhiko

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Y1 - 2007/10/26

N2 - (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.

AB - (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.

KW - C-C activation

KW - Esters

KW - Indium

KW - Retro reactions

KW - Synthetic methods

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ER -

Indium-catalyzed retro-claisen condensation

Abstract

Keywords

ASJC Scopus subject areas

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