Issue 52, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
17 Yan 2017
Accepted
07 Kho 2017
First published
08 Kho 2017

Chem. Commun., 2017,53, 7092-7095

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, 53, 7092 DOI: 10.1039/C7CC01285C

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