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Issue 52, 2017
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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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Article information


Submitted
17 Feb 2017
Accepted
07 Jun 2017
First published
08 Jun 2017

Chem. Commun., 2017,53, 7092-7095
Article type
Communication

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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