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

TY - JOUR

T1 - Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids

AU - Stuhr-Hansen, Nicolai

AU - Padrah, Shahrokh

AU - Strømgaard, Kristian

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - Depsipeptides

KW - Diazotization

KW - Hydroxylation

KW - α-Hydroxy carboxylic acids

U2 - 10.1016/j.tetlet.2014.05.090

DO - 10.1016/j.tetlet.2014.05.090

M3 - Journal article

AN - SCOPUS:84904071351

SN - 0040-4039

VL - 55

SP - 4149

EP - 4151

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -