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

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 tr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-06, Vol.53 (52), p.7092-7095
Main Authors: Faria, E N, Jupp, A R, Goicoechea, J M
Format: Article
Language:English
Subjects:
Amino acids
Anions
Bearing
Formations
Phosphines
Transformations
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc01285c