150618-33-0Relevant academic research and scientific papers
Transamination of Fluorinated β-Keto Carboxylic Esters. A Biomimetic Approach to β-Polyfluoroalkyl-β-amino Acids.
Soloshonok, Vadim A.,Kirilenko, Alexander G.,Kukhar', Valery P.,Resnati, Giuseppe
, p. 3621 - 3624 (1993)
The base-catalyzed isomerization of N-benzylimines (or enamines) of β-polyfluoroalkyl-β-ketocarboxylic esters cleanly affords the N-benzylidene derivatives of β-polyfluoro-β-aminocarboxylic esters which are hydrolyzed to corresponding amino acids in high overall yields.
Biomimetic base-catalyzed [1,3]-proton shift reaction. A practical synthesis of β-fluoroalkyl-β-amino acids
Soloshonok, Vadim A.,Kukhar, Valery P.
, p. 6953 - 6964 (2007/10/03)
An efficient approach to practical synthesis of β-fluoroalkyl-β-amino acids is described. The method consists in the reducing reagent-free base-catalyzed biomimetic transamination between fluorinated β-keto carboxylic esters and benzylamine. This transformation involves two sequential base-catalyzed [1,3]-proton transfers giving rise to corresponding N-benzylidene derivatives as the products of final thermodynamic equilibration, directed by the electron-withdrawing character of fluoroalkyl groups. Opportunity for catalytic enantiocontrolled synthesis of targeted β-amino acids with application of monochiral base, as a catalyst for these isomerizations, is demonstrated.
Fluorinated diaminobutane derivatives
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, (2008/06/13)
Fluorinated diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: STR1 wherein: R1 represents hydrogen, C1 -C6 alkyl, or phenyl-(C1 -C4 alkyl); R2 represents hydrogen, C1 -C6 alkyl, phenyl-(C1 -C4 alkyl), or R4, where R4 is as defined below; R3 represents hydrogen, or, except when R2 represents R4, R4, where R4 is as defined below; each R4, independently, represents C2 -C5 alkylcarbonyl, phenylcarbonyl, phenyl-(C1 -C4 alkyl) carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of an L-aminocarboxylic acid; and p represents 1 or 2, and pharmaceutically acceptable acid addition salts thereof.
