150618-25-0Relevant academic research and scientific papers
Easy synthesis of (E)- or (Z)-perfluorinated β-enaminaoesters
Prié, Gildas,Richard, Sébastien,Parrain, Jean-Luc,Duchêne, Alain,Abarbri, Mohamed
, p. 35 - 41 (2002)
(E)- or (Z)-perfluorinated β-enaminoesters were prepared by direct addition of primary or secondary amines to ethyl perfluoroalkynoates without any catalyst.
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.
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 (2007/10/02)
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.
