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Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids

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Abstract

We describe the reactivity of the 2-phosphaethynolate anion (PCO) towards enantiomerically pure α-amino acids (AAs) resulting in the formation of novel salts of phosphinecarboxamides bearing chiral functionalities. These transformations occurred quantitatively with all but one of the amino acids trialled (the basic amino acid arginine was found to be unreactive). The resulting ionic species can be readily protonated to afford N-(phosphanyl)carbonyl-amino acids, a novel group of amino acids bearing primary phosphine functionalities.

Graphical abstract: Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids

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Publication details

The article was received on 17 Feb 2017, accepted on 07 Jun 2017 and first published on 08 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC01285C
Citation: Chem. Commun., 2017, Advance Article
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    Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids

    E. N. Faria, A. R. Jupp and J. M. Goicoechea, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01285C

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