Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters

A novel tactic to synthesize unsymmetrical 3-aryladipic acid esters has been developed via magnesium-promoted reductive coupling of ethyl cinnamates with methyl acrylate. In the present methodology, 3-aryladipic acid derivatives were prepared with good functional group tolerance and a wide substrate...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 22; pp. 15894 - 15901
Main Authors Zhang, Tianyuan, Zhang, Jiawu, Mori, Akihiro, Morii, Taku, Kuramochi, Keisuke, Maekawa, Hirofumi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.11.2023
American Chemical Society (ACS)
Amer Chemical Soc
Subjects
adipic acid
Chemistry
Chemistry, Organic
cinnamates
magnesium
organic chemistry
Physical Sciences
regioselectivity
Science & Technology
CINNAMIC ACID
CYCLOHEXANE
DERIVATIVES
EFFICIENT
DIRECT OXIDATION
SILYLATION
Online AccessGet full text

Cover

More Information
Summary:A novel tactic to synthesize unsymmetrical 3-aryladipic acid esters has been developed via magnesium-promoted reductive coupling of ethyl cinnamates with methyl acrylate. In the present methodology, 3-aryladipic acid derivatives were prepared with good functional group tolerance and a wide substrate scope under very mild reaction conditions in good yields. The application of this reaction to dienic acid esters led to the successful control of the reaction to give 5-aryl-oct-3-enedioic acid esters with high regioselectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01982