Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids

Research output: Contribution to journalJournal articleResearchpeer-review

Nicolai Stuhr-Hansen, Shahrokh Padrah, Kristian Strømgaard

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 languageEnglish
JournalTetrahedron Letters
Volume55
Issue number30
Pages (from-to)4149-4151
Number of pages3
ISSN0040-4039
DOIs
Publication statusPublished - 2014

    Research areas

  • Depsipeptides, Diazotization, Hydroxylation, α-Hydroxy carboxylic acids

ID: 120136021