85231-78-3Relevant academic research and scientific papers
Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water
Da?ková, Vanda,Buter, Jeffrey,Schoonen, Anne K.,Lutz, Martin,de Vries, Folkert,Feringa, Ben L.
supporting information, p. 11120 - 11126 (2021/04/09)
The origin of biomolecular homochirality continues to be one of the most fascinating aspects of prebiotic chemistry. Various amplification strategies for chiral compounds to enhance a small chiral preference have been reported, but none of these involves phosphorylation, one of nature's essential chemical reactions. Here we present a simple and robust concept of phosphorylation-based chiral amplification of amines and amino acids in water. By exploiting the difference in solubility of a racemic phosphoramidate and its enantiopure form, we achieved enantioenrichment in solution. Starting with near racemic, phenylethylamine-based phosphoramidates, ee's of up to 95 % are reached in a single amplification step. Particularly noteworthy is the enantioenrichment of phosphorylated amino acids and their derivatives, which might point to a potential role of phosphorus en-route to prebiotic homochirality.
Synthesis of α-arylalkylamines by addition of Grignard reagents to N- (diethoxyphosphoryl)aldimines
Zwierzak, Andrzej,Napieraj, Anna
, p. 930 - 934 (2007/10/03)
Addition of organomagnesium bromides to N-(diethoxyphosphoryl) aldimines 1 carded out in tetrahydrofuran at 20-25°C affords diethyl N-alkyl- phosphoramidates 2a-w in high yields and spectroscopic purity. Deprotection of the latent amino groups in 2 results in the formation of α-arylalkylamine hydrochlorides 3a-w.
Phosphoramidate-mediated conversion of metal carbonyls into metal isonitriles
Gibson, Susan E.,Hinkamp, Thomas W.,Peplow, Mark A.,Ward, Mark F.
, p. 1671 - 1672 (2007/10/03)
The reaction of metal carbonyls with readily-available phosphoramidate anions provides a new route to metal isonitriles; in particular, enantiomerically pure isonitrile complexes are easily accessed by this method.
