150618-36-3Relevant academic research and scientific papers
HOMOCHIRAL HETEROORGANIC ANALOGS OF NATURAL COMPOUNDS. II. 3-AMINO-4,4,4-TRIFLUOROBUTYRIC ACID: SYNTHESIS, ENZYMATIC RESOLUTION, AND DETERMINATION OF THE ABSOLUTE CONFIGURATIONS OF THE ENANTIOMERS
Kukhar', V. K.,Soloshonok, V. A.,Shvyadas, V. K.,Kotik, N. V.,Galaev, I. Yu,et al.
, p. 233 - 235 (2007/10/02)
Homochiral (R)- and (S)-3-amino-4,4,4-trifluorobutyric acids, not previously described, have been obtained.The synthesis of racemic 3-amino-4,4,4-trifluorobutyric acid was performed by a three-stage scheme from methyl 4,4,4-trifluoroacetoacetate and benzylamine.The racemic acid was resolved into enantiomers by means of the enantioselective hydrolysis of the corresponding phenylacetyl derivatives with penicillin acylase.It has been established on the basis of an x-ray structural investigation that the (-)-enantiomer has the (S)-absolute configuration of the chiral carbon atom.The specific optical rotations (D25, 1percent, 6N HCl) for the preparations of the (R)- and (S)-3-amino-4,4,4-trifluorobutyric acid that were obtained were determined as +27.6 and -27.2 deg, respectively.
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.
