871315-40-1Relevant articles and documents
Catalytic asymmetric 1,2-addition of α-isothiocyanato phosphonates: Synthesis of chiral β-hydroxy- or β-amino-substituted α-amino phosphonic acid derivatives
Cao, Yi-Ming,Shen, Fang-Fang,Zhang, Fu-Ting,Zhang, Jin-Long,Wang, Rui
, p. 1862 - 1866 (2014)
α-Amino phosphonic acid derivatives are considered to be the most important structural analogues of α-amino acids and have a very wide range of applications. However, approaches for the catalytic asymmetric synthesis of such useful compounds are very limited. In this work, simple, efficient, and versatile organocatalytic asymmetric 1,2-addition reactions of α-isothiocyanato phosphonate were developed. Through these processes, derivatives of β-hydroxy-α-amino phosphonic acid and α,β-diamino phosphonic acid, as well as highly functionalized phosphonate-substituted spirooxindole, can be efficiently constructed (up to 99 % yield, d.r. >20:1, and >99 % ee). This novel method provides a new route for the enantioselective functionalization of α-phosphonic acid derivatives. Correct chirality critical: Organocatalytic asymmetric Adol-type and Mannich-type reactions of α-isothiocyanato phosphonate have been realized. Michael addition was also applicable under the same catalytic conditions. This versatile approach provides a new route for the synthesis of diverse highly optically active functionalized α-amino phosphonic acid derivatives. Copyright
Bis{phenyl[di(methoxyethyloxy)phosphoryl]methyl}amine as a new ligand for metal ions and cationic organic molecules
M?ynarz, Piotr,Ptak, Tomasz,Czernicka, Anna,Pankiewicz, Rados?aw,Gluza, Karolina,Zarzeczańska, Dorota
experimental part, p. 18 - 23 (2011/05/04)
The bis(phenylphosphorylmethyl)amine containing binding units based on "crown-ether like" ester moiety was tested as a supramolecular host molecule. The complexation properties towards metal ions (Li+, Na+, K+, Rb+, Cs+, Mg2+, Ca2+, Ba2+) and hydrochlorides of amino acids (Lys, Arg), diethylenetriamine (2EN3A) and pentaethylenehexaamine (5EN6A) were studied. In order to assess the binding affinities of the receptor to selected guest molecules in various solvents, the ESI-MS and NMR techniques were applied. The results were also supported by theoretical studies. The ESI-MS studies revealed the selective binding of Cs+ and 5EN6 by the phosphonate molecule, whereas NMR investigation in solution indicated tighter association of the host-guest system obtained for Mg2+ and Arg. The discrepancies between the results originating from both used methods are most likely caused by influence of the solvent on intermolecular interactions.