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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids
Aleksi E K Eronen1, Jere K Mannisto1, Karina Moslova1
1Department of Chemistry, University of Helsinki, A.I. Virtasenaukio 1, 00014 Helsinki, Finland.
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 δ-lactones.
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