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

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids. / Stuhr-Hansen, Nicolai; Padrah, Shahrokh; Strømgaard, Kristian.

In: Tetrahedron Letters, Vol. 55, No. 30, 2014, p. 4149-4151.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Stuhr-Hansen, N, Padrah, S & Strømgaard, K 2014, 'Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids', Tetrahedron Letters, vol. 55, no. 30, pp. 4149-4151. https://doi.org/10.1016/j.tetlet.2014.05.090

APA

Stuhr-Hansen, N., Padrah, S., & Strømgaard, K. (2014). Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids. Tetrahedron Letters, 55(30), 4149-4151. https://doi.org/10.1016/j.tetlet.2014.05.090

Vancouver

Stuhr-Hansen N, Padrah S, Strømgaard K. Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids. Tetrahedron Letters. 2014;55(30):4149-4151. https://doi.org/10.1016/j.tetlet.2014.05.090

Author

Stuhr-Hansen, Nicolai ; Padrah, Shahrokh ; Strømgaard, Kristian. / Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 30. pp. 4149-4151.

Bibtex

@article{884297f9216540678b12c153359db2b3,
title = "Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids",
abstract = "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.",
keywords = "Depsipeptides, Diazotization, Hydroxylation, α-Hydroxy carboxylic acids",
author = "Nicolai Stuhr-Hansen and Shahrokh Padrah and Kristian Str{\o}mgaard",
year = "2014",
doi = "10.1016/j.tetlet.2014.05.090",
language = "English",
volume = "55",
pages = "4149--4151",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Pergamon Press",
number = "30",

}

RIS

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

VL - 55

SP - 4149

EP - 4151

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 30

ER -

ID: 120136021