82629-22-9Relevant articles and documents
The Synthesis of α-Aminophosphonates via Enantioselective Organocatalytic Reaction of 1-(N-Acylamino)alkylphosphonium Salts with Dimethyl Phosphite
Ku?nik, Anna,Pa?dzierniok-Holewa, Agnieszka,Stecko, Sebastian,Wal?cka-Kurczyk, Alicja,Walczak, Krzysztof
, (2020/01/28)
α-Aminophosphonic acids are phosphorus analogues of α-amino acids. Compounds of this type find numerous applications in medicine and crop protection due to their unique biological activities. A crucial factor in these activities is the configuration of the stereoisomers. Only a few methods of stereoselective transformation of α-amino acids into their phosphorus analogues are known so far and all of them are based on asymmetric induction, thus involving the use of a chiral substrate. In contrast, we have focused our efforts on the development of an effective method for this type of transformation using a racemic mixture of starting N-protected α-amino acids and a chiral catalyst. Herein, a simple and efficient stereoselective organocatalytic α-amidoalkylation of dimethyl phosphite by 1-(N-acylamino)alkyltriphenylphosphonium salts to enantiomerically enriched α-aminophosphonates is reported. Using 5 mol% of chiral quinine- or hydroquinine-derived quaternary ammonium salts provides final products in very good yields up to 98% and with up to 92% ee. The starting phosphonium salts were easily obtained from α-amino acid derivatives by decarboxylative methoxylation and subsequent substitution with triphenylphosphonium tetrafluoroborate. The appropriate self-disproportionation of enantiomers (SDE) test for selected α-aminophosphonate derivatives via achiral flash chromatography was performed to confirm the reliability of the enantioselectivity results that were obtained.
Comparative studies on the amidoalkylating properties of N-(1-methoxyalkyl)amides and 1-(N-acylamino)alkyltriphenylphosphonium salts in the michaelis-arbuzov-like reaction: A new one-pot transformation of N-(1-methoxyalkyl)amides into phosphonic or phosphinic analogs of N-Acyl-α-amino acids
Adamek, Jakub,Pazdzierniok-Holewa, Agnieszka,Zielinska, Katarzyna,Mazurkiewicz, Roman
, p. 967 - 980 (2013/08/23)
It was demonstrated that N-(1-methoxyalkyl)amides do not react with trimethyl phosphite under neutral or basic conditions. The treatment of N-(1-methoxyalkyl)amides with trialkyl phosphites or dialkyl phosphonites, triphenylphosphonium tetrafluoroborate, and Huenig's base caused immediate formation of the corresponding 1-(N-acylamino)-alkyltriphenylphosphonium tetrafluoroborates, followed by the slow Michaelis-Arbuzov-like reaction of phosphonium salt with phosphites or phosphonites to α-(N-acylamino)- alkanephosphonic or α-(N-acylamino)alkanephosphinic acid esters, respectively. A plausible mechanism of the considered transformations, assuming an equilibrium between N-(1-alkoxyalkyl)amide, triphenylphosphonium tetrafluoroborate, 1-(N-acylamino)alkyltriphenyl-phosphonium salt, N-acylimine, and N-acyliminium salts, is discussed.
Synthesis and activity study of phosphonamidate dipeptides as potential inhibitors of VanX
Yang, Ke-Wu,Cheng, Xu,Zhao, Chuan,Liu, Cheng-Cheng,Jia, Chao,Feng, Lei,Xiao, Jian-Min,Zhou, Li-Sheng,Gao, Hui-Zhou,Yang, Xia,Zhai, Le
supporting information; experimental part, p. 7224 - 7227 (2012/02/02)
In an effort to develop inhibitors of VanX, the phosphonamidate analogs of d-Ala-d-Ala dipeptides, N-[(1-aminoethyl) hydroxyphosphinyl]-glycine (1a), -alanine (1b), -valine (1c), -leucine (1d) and -phenylalanine (1e) were synthesized, characterized and ev
