- 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.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
- Version:
- Accepted manuscript
- Files:
-
-
(pdf, 300.4KB)
-
- Publisher copy:
- 10.1039/c7cc01285c
-
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- Funding agency for:
- Jupp, AR
- Publisher:
- Royal Society of Chemistry Publisher's website
- Journal:
- Chemical Communication Journal website
- Volume:
- 53
- Issue:
- 52
- Pages:
- 7092-7095
- Publication date:
- 2017-06-08
- Acceptance date:
- 2017-06-07
- DOI:
- EISSN:
-
1364-548X
- ISSN:
-
1359-7345
- Pubs id:
-
pubs:702389
- URN:
-
uri:e1b8a40f-c388-47d4-bf2d-6989c7fcaa9e
- UUID:
-
uuid:e1b8a40f-c388-47d4-bf2d-6989c7fcaa9e
- Local pid:
- pubs:702389
- Language:
- English
- Copyright holder:
- © Faria, Jupp, & Goicoechea, 2017
- Copyright date:
- 2017
- Notes:
- This is the author accepted manuscript following peer review version of the article. The final version is available online from Royal Society of Chemistry at: 10.1039/c7cc01285c
Journal article
Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids
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+ Engineering and Physical Sciences Research Council
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Conselho Nacional de Desenvolvimento
Cientı´fico e Tecnolo´gico
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