Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids
Research output: Contribution to journal › Journal article › Research › peer-review
An effective and improved procedure is developed for the synthesis of α-hydroxy carboxylic acids by treatment of the corresponding protonated α-amino acid with tert-butyl nitrite in 1,4-dioxane-water. The amino moiety must be protonated and located α to a carboxylic acid function in order to undergo initial diazotization and successive hydroxylation, since neither β-amino acids nor acid derivatives such as esters and amides undergo hydroxylations. The method is successfully applied for the synthesis of 18 proteinogenic amino acids.
Original language | English |
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Journal | Tetrahedron Letters |
Volume | 55 |
Issue number | 30 |
Pages (from-to) | 4149-4151 |
Number of pages | 3 |
ISSN | 0040-4039 |
DOIs | |
Publication status | Published - 2014 |
- Depsipeptides, Diazotization, Hydroxylation, α-Hydroxy carboxylic acids
Research areas
ID: 120136021