128948-79-8Relevant academic research and scientific papers
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.
Enantioselective synthesis of H -phosphinic acids bearing natural amino acid residues
Yao, Qiuli,Yuan, Chengye
, p. 6962 - 6974 (2013/08/23)
The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butanesulfinyl imines. Good yields a
An easy entry to optically active α-amino phosphonic acid derivatives using phase-transfer catalysis (PTC)
Fini, Francesco,Micheletti, Gabriele,Bernardi, Luca,Pettersen, Daniel,Fochi, Mariafrancesca,Ricci, Alfredo
supporting information; experimental part, p. 4345 - 4347 (2009/03/12)
The unprecedented use of phase-transfer catalysis (PTC) in an asymmetric hydrophosphonylation reaction allows the obtainment of a range of optically active α-amino phosphonic acid derivatives directly from α-amido sulfones. The Royal Society of Chemistry.
Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids
Joly, Guy D.,Jacobsen, Eric N.
, p. 4102 - 4103 (2007/10/03)
Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free α-amino phosphonic acids in highly enantioenriched form. Copyright
Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation
Burk, Mark J.,Stammers, Timothy A.,Straub, Judith A.
, p. 387 - 390 (2008/02/11)
(equation presented) Cationic rhodium catalysts of the C2 symmetric DuPHOS (1) and BPE (2) ligands have demonstrated the ability to asymmetrically hydrogenate a novel series of enol phosphonates (3) in good to excellent enantiomeric excess unde
Potent Inhibition of Pepsin and Penicillopepsin by Phosphorus-Containing Peptide Analogues
Bartlett, Paul A.,Hanson, John E.,Giannousis, Peter P.
, p. 6268 - 6274 (2007/10/02)
Phosphinic and phosphonic acid peptide derivatives have been evaluated as inhibitors of the aspartic proteases pepsin and penicillopepsin.The most potent of those studied is isovaleryl-Val-Val-LeuP-(O)Phe-Ala-Ala-OMe (4) (LeuP repres
