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Syntheses of the (±)-, (+)-, and (−)-forms of 2-Amino-3-(8-hydroxyquinolin-3-yl)propanoic acid (8HQ-3Ala) from a common dehydroamino acid methyl ester precursor
Citation
Banwell, MG and Schwartz, BD and Bissember, AC and Herlt, T and Willis, AC and Gardiner, MG and Illesinghe, J and Robinson, AJ, Syntheses of the ( )-, (+)-, and (−)-forms of 2-Amino-3-(8-hydroxyquinolin-3-yl)propanoic acid (8HQ-3Ala) from a common dehydroamino acid methyl ester precursor, Asian Journal of Chemistry, 11, (4) pp. e202100455. ISSN 0970-7077 (2021) [Refereed Article]
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DOI: doi:10.1002/ajoc.202100455
Abstract
The (±)-, (+)- and (−)-forms of 2-amino-3-(8-hydroxyquinolin-3-yl)-propanoic acid (1 or 8HQ-3Ala) have been prepared from o-methoxyacetanilide. A combination of Vilsmeier-Haack, Erlenmeyer-Plöchl and methanolysis reactions was used to convert the starting material into the Z-configured dehydroamino acid derivative 5. Catalytic hydrogenation of the latter compound then gave, after reductive dechlorination and demethylation steps, compound (±)-1 ⋅ 2TFA. Asymmetric hydrogenation of compound 5 using a rhodium precatalyst and an enantiopure DuPhos-type ligand selectively delivered either acid (+)-1 or (−)-1.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | amino acid, asymmetric hydrogenation, Erlenmeyer-Plöchl reaction, 8-hydroxyquinoline |
| Research Division: | Chemical Sciences |
| Research Group: | Organic chemistry |
| Research Field: | Organic chemical synthesis |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding knowledge |
| Objective Field: | Expanding knowledge in the chemical sciences |
| UTAS Author: | Bissember, AC (Associate Professor Alex Bissember) |
| ID Code: | 149879 |
| Year Published: | 2021 |
| Deposited By: | Chemistry |
| Deposited On: | 2022-04-21 |
| Last Modified: | 2022-05-05 |
| Downloads: | 0 |
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