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Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides.

ABSTRACT: An N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aromatic aldehydes with N-substituted itaconimides has been developed. A delicate balance between the Stetter reaction and the competing isomerization of the itaconimide double bond has been achieved in this operationally simple reaction to afford valuable new succinimide derivatives containing 1,4 and 1,5 dicarbonyl scaffolds in good to excellent yields. The reaction tolerates variable substituents on both aldehydes and N-substituted itaconimides.

SUBMITTER: Ahire MM

PROVIDER: S-EPMC6644805 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with <i>N</i>-Substituted Itaconimides.

Ahire Milind M MM Mhaske Santosh B SB

ACS omega 20171011 10

An N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aromatic aldehydes with <i>N</i>-substituted itaconimides has been developed. A delicate balance between the Stetter reaction and the competing isomerization of the itaconimide double bond has been achieved in this operationally simple reaction to afford valuable new succinimide derivatives containing 1,4 and 1,5 dicarbonyl scaffolds in good to excellent yields. The reaction tolerates variable substituents on both aldehydes a ...[more]

PMID: 31457257

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