135950-37-7Relevant academic research and scientific papers
ASYMMETRIC SYNTHESIS OF HETEROORGANIC ANALOGS OF NATURAL COMPOUNDS. 3. GENERAL PREPARATIVE METHOD OF DIASTEREO- AND ENANTIOSELECTIVE SYNTHESIS OF FLUORINE-CONTAINING 2(R),3(S)-β-PHENYLSERINES
Soloshonok, V. A.,Kukhar, V. P.,Galushko, S. V.,Kolycheva, M. T.,Rozhenko, A. B.,Belokon, Yu. N.
, p. 1046 - 1054 (1991)
The diastereo- and enantioselective synthesis of the previously unknown 2(R),3(S)-β-phenylserines containing fluorine atoms, the O-CHF2-, O-CF3-, and CF3 groups in the benzene ring, was carried out by alkylation of a Ni(II) complex of a Schiff base of glycine with (S)-2-N-(N'-benzylprolyl)aminobenzophenone by fluorine-substituted benzaldehydes.The factors influencing the stereochemical result of the reactions studied are not the steric characteristics of the substituents in benzaldehydes, but their electronic nature.
General Method for the Synthesis of Enantiomerically Pure β-Hydroxy-α-amino Acids, containing Fluorine Atoms in the Side Chains. Case of Stereochemical Distinction between Methyl and Trifluoromethyl Groups. X-Ray Crystal and Molecular Structure of the Nickel(II) Complex of ...
Soloshonok, Vadim A.,Kukhar, Valeri P.,Galushko, Sergei V.,Svistunova, Nataly Yu.,Avilov, Dimitri V.,et al.
, p. 3143 - 3156 (2007/10/02)
The chiral NiII complex 1 of a Schiff's base derived from (S)-o-benzophenone (BPB) and glycine was treated with fluoro-substituted aldehydes (aliphatic and aromatic) in MeOH or CHCl3.The addition proceeds with high diastereoselectivity to give, if catalysed by MeONa in MeOH, the corresponding complexes of syn-(2R)-3-fluorophenylserines (84-100percent) d.e.) and syn-(2S)-fluoroalkylserines (90percent d.e.), and, if catalysed by NEt3 or DABCO (MeOH or CHCl3), the corresponding complexes of syn-(2S)-, and anti-(2S)-3-fluorophenylserines and fluoroalkylserines.The second-order asymmetric transformation may be successfully employed to obtain diastereoisomerically pure complexes of anti-(2R)-3-fluorophenylserines.Condensation of trifluoroacetone with complex 1, catalysed by MeONa, gave predominantly (at least >95percent d.e.) the diastereoisomeric complex, containing (2S,3S)-β-(trifluoromethyl)threonine, as shown by an X-ray diffraction structural study.Diastereoisomerically and enantiomerically pure fluorine-containing 3-phenyl- and 3-alkyl-serines were obtained from the corresponding diastereomerically pure complexes, separated by chromatography or crystallization.The initial chiral auxiliary BPB was recovered (80-98percent).The influence of the reaction's conditions and the nature of the corresponding fluoro-substituted aldehydes on the diastereoselectivity of the reactions is discussed.
