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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.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1039/c7cc01285c

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Department:
Oxford, MPLS, Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry
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Author
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Department:
Lady Margaret Hall
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Author
Conselho Nacional de Desenvolvimento Cientı´fico e Tecnolo´gico More from this funder
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

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