17049-78-4Relevant academic research and scientific papers
Synthesis of the First Stable Phosphonamide Transition State Analogue
De Medina,Ingrassia,Mulliez
, p. 8424 - 8430 (2003)
Three methods were selected for the one-pot synthesis of the fully protected β-fluoroaminophosphonic acids, using the readily accessible N-protected β-fluoroaminals. These were activated by acylation leading, by β-elimination, to a transient N-acylimine immediately trapped by reactive forms of dialkyl phosphites. Avoiding basic conditions, the complete or partial deprotection of these N-protected β-fluoroaminophosphonic esters allowed the synthesis of the free amino acids, their esters, and a racemic β-trifluorophosphonamidic acid. The latter, which represents a transition state analogue formed by the bacterial transpeptidase, is perfectly stable at pH 4.7, contrary to the nonfluorinated compounds.
Synthesis of α-trifluoromethyl-α-hydroxycarboxylate dervatives and their phosphorus-containing analogs with the use of fluorinated diazo compounds
Titanyuk,Vorob'eva,Osipov,Beletskaya
experimental part, p. 619 - 623 (2010/10/04)
Approach was developed underlain by the use of fluorinated diazocompounds to the synthesis of derivatives of α-trifluoromethyl-α- hydroxycarboxylic acids and their phosphorus-containing analogs, α-trifluoromethyl-α-hydroxyphosphonic acids. Methyl 2-diazo-3,3,3-trifluoropropionate and diethyl 1-diazo-2,2,2- trifluoroethylphosphonate under the action of catalytic quantities of dirhodium tetraacetate Rh2(OAc)4 easily inserted into the O-H bond leading to the formation of the corresponding products in high yields. Pleiades Publishing, Ltd., 2010.
