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.
Highlights
The development of biomass-based economy is creating an abundant amount of protein waste which can be processed into amino acids
All chemicals were obtained from commercial sources
Phenylpyruvic acid, cinnamaldehyde, 1-propanol, 1-butanol, tert-butanol, and substituted aromatic aldehydes were all purchased from Sigma-Aldrich and used without further purification
Summary
The development of biomass-based economy is creating an abundant amount of protein waste which can be processed into amino acids. In advanced biorefinery concepts, amino acids are further transformed into nitrogen-containing platform chemicals, such as caprolactam.− Amino acids have been extensively studied during the last 200 years, yet continue to be a source of new reactivity. Amino acids are further transformed into nitrogen-containing platform chemicals, such as caprolactam.− Amino acids have been extensively studied during the last 200 years, yet continue to be a source of new reactivity Regardless of their well-established chemistry, to better utilize the available amino acids as synthetic precursors for value-added chemicals, new types of reactions are sought-after.. Regardless of their well-established chemistry, to better utilize the available amino acids as synthetic precursors for value-added chemicals, new types of reactions are sought-after.4,5 In this respect, we report here a straightforward method for preparing previously unreported aryl-substituted hydroxy dicarboxylic acids (from hereon diacids) from various amino acids. We report here a straightforward method for preparing previously unreported aryl-substituted hydroxy dicarboxylic acids (from hereon diacids) from various amino acids These diacids are formed with up to four stereogenic centers in a diastereospecific manner. We took an initiative to carry out further studies and reveal mechanistic details of diacid synthesis
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