Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acidsElectronic supplementary information (ESI) available: Full experimental details including spectra and computational data. CCDC 1533100. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7cc01285c

• Main Authors: Faria, E. N, Jupp, A. R, Goicoechea, J. M
• Format: Article
• Language: English
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c7cc01285c

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. 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.