85231-78-3Relevant articles and documents
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.
