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Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids.

ABSTRACT: Herein we report a unique method for preparing diaryl hydroxyl dicarboxylic acids in a diastereospecific manner. The three-component reaction occurs between amino acid, aromatic aldehyde, and primary alcohol in alkaline solutions under microwave-assisted conditions. The dicarboxylic acids are isolated as sodium salts in high yields (up to 77%) by direct precipitation from the reaction solution. The experimental results suggest that the diastereospecificity originates from a [3,3]-sigmatropic rearrangement followed by a sodium-assisted hydride transfer. As further shown, the previously unreported dicarboxylic acids are easily turned into corresponding ?-lactones.

SUBMITTER: Eronen AEK

PROVIDER: S-EPMC7497638 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids.

Eronen Aleksi E K AEK Mannisto Jere K JK Moslova Karina K Nieger Martin M Heliövaara Eeva E Repo Timo T

The Journal of organic chemistry 20200310 9

Herein we report a unique method for preparing diaryl hydroxyl dicarboxylic acids in a diastereospecific manner. The three-component reaction occurs between amino acid, aromatic aldehyde, and primary alcohol in alkaline solutions under microwave-assisted conditions. The dicarboxylic acids are isolated as sodium salts in high yields (up to 77%) by direct precipitation from the reaction solution. The experimental results suggest that the diastereospecificity originates from a [3,3]-sigmatropic rea ...[more]

PMID: 32126166

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