Decarboxylative Amination of SMAHOs by Dialkyl Azodicarboxylates

The decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates is described. The reaction was promoted by 1,4‐diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst in heated toluene. High yields of the coupling products were generally obtained, and the...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-04, Vol.27 (16), p.n/a
Main Authors: Pinaud, Marine, Gall, Erwan Le, Presset, Marc
Format: Article
Language:English
Subjects:
amination
aminoacid
decarboxylation
organocatalysis
SMAHO
Toluene
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Summary:The decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates is described. The reaction was promoted by 1,4‐diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst in heated toluene. High yields of the coupling products were generally obtained, and the scope of the reaction proved rather important with the potential presence of functionalized side chains at the α‐position, affording an original access to α‐aminoester derivatives. The organocatalyzed decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates led to the formation of α‐aminoester derivatives. The reaction can be performed under mild reaction conditions using 1,4‐diazabicyclo[2.2.2]octane (DABCO) as a catalyst and displayed a rather important scope.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400128