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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
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