625093-77-8Relevant academic research and scientific papers
1-Trifluoromethyl-1-diethoxyphosphoryl carbene: A new synthon for the preparation of CF3-containing α-hydroxy and α-amino phosphonic acid derivatives
Titanyuk, Igor D.,Vorob'eva, Daria V.,Osipov, Sergej N.,Beletskaya, Irina P.
, p. 1355 - 1358 (2006)
The first synthesis of diethyl 1-diazo-2,2,2-trifluoroethylphosphonate has been developed starting from readily available compounds. The synthetic utility of this compound is demonstrated via its Rh-catalyzed insertion into O-H and N-H bonds to produce CF3-substituted α-hydroxy phosphonic and α-amino, phosphonic acid derivatives. Georg Thieme Verlag Stuttgart.
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.
A new preparative method for the synthesis of diethyl 1-diazo-2,2,2- trifluoroethylphosphonate via an imino phosphonate
Karimova,Vorobyeva,Shchetnikov,Osipov
, p. 107 - 109 (2011/01/08)
A preparative method for the synthesis of diethyl 1-diazo-2,2,2- trifluoroethylphosphonate from trifluoroacetic anhydride and benzyl carbamate via diethyl 1-benzyloxycarbonylimino-2,2,2-trifluoroethylphosphonate is developed. Optimum conditions for the ch
Synthesis of the First Stable Phosphonamide Transition State Analogue
De Medina,Ingrassia,Mulliez
, p. 8424 - 8430 (2007/10/03)
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.
