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

Xianjun Xu | Zendy; Liliang Huang | Zendy; Xiaoying Yin | Zendy; Erik V. Van der Eycken | Zendy; Huangdi Feng | Zendy

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

Author(s) -

Xianjun Xu,

Liliang Huang,

Xiaoying Yin,

Erik V. Van der Eycken,

Huangdi Feng

Publication year - 2018

Publication title -

organic chemistry frontiers

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.377

H-Index - 56

eISSN - 2052-4129

pISSN - 2052-4110

DOI - 10.1039/c8qo00919h

Subject(s) - desymmetrization , chemistry , alkyl , conjugate , organic chemistry , medicinal chemistry , catalysis , enantioselective synthesis , mathematical analysis , mathematics

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.

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