Issue 20, 2018

Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

Abstract

A novel method has been developed for the desymmetrization of aromatic dicarboxylic acids by employing an esterification reaction/conjugate addition of a carboxyl group to ynoates, which can trigger a coupling reaction. This one-pot cascade transformation, utilizing trialkylamines as alkyl sources for esterification, and ethyl propiolate as a protective or coupling reagent for carboxyl functions (hydrolysis, amidation, esterification, and thioesterification), leads to an asymmetric dicarbonyl target skeleton in a selective manner.

Graphical abstract: Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

Supplementary files

Article information

Article type
Research Article
Submitted
24 aug 2018
Accepted
12 sep 2018
First published
13 sep 2018

Org. Chem. Front., 2018,5, 2955-2959

Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

X. Xu, L. Huang, X. Yin, E. V. Van der Eycken and H. Feng, Org. Chem. Front., 2018, 5, 2955 DOI: 10.1039/C8QO00919H

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