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The influence of molecular structure and crystallization time on the efficiency of diastereoisomeric salt forming resolutions
Reciprocal resolutions between compounds (racemates and enantiomers) with similar structures have been examined. Amongst structurally similar compounds (so called relative structures) several N-acyl amino acids and amino acid esters were investigated. A part of the resolving agent or the racemic compound could be replaced by an achiral compound with a relative structure and an additive could occasionally improve significantly the efficiency of the resolution. Both the kinetic and the thermodynamic controls were observed as governing factors of the reciprocal resolutions.
Palovics, Emese,Schindler, Jozsef,Faigl, Ferenc,Fogassy, Elemer
experimental part
p. 2429 - 2434
(2010/12/25)

Optical resolution of N-formylphenylalanine succeeds by crystal growth rate differences of diastereomeric salts
Optical resolution of racemic-phenylalanine through its N-formyl derivative with a 1-phenylethylamine resolving agent is an effective procedure. Differential scanning calorimetry, single crystal X-ray diffraction and optical microscopy were used in the investigation of the resolution process. It was found that the thermodynamic properties of the given system would not allow the efficient enantiomer separation. Kinetic effects during the crystal formation have been discovered by the comparison of the crystal morphologies of the two diastereomers. The crystal structure of the less soluble diastereomer (S)-(-)-1-phenylethylammonium (S)-(+)-N-formylphenylalaninate salt has been determined and discussed.
Bereczki, Laura,Palovics, Emese,Bombicz, Petra,Pokol, Gyoergy,Fogassy, Elemer,Marthi, Katalin
p. 260 - 264
(2007/10/03)

Solvent dependency though not solvate formation in the derivative-derivative resolution of N-formylphenylalanine
The efficiency of the resolution of N-formylphenylalanine was remarkably improved using (S)-(+)-2-benzylaminobutanol resolving agent in acetone. The efficiency of the resolution strongly depended on the quality of the solvent. Nevertheless, solvate formation did not occur during the process. The nature of the solvent-dependence was studied. The solid-melt binary phase diagram of the diastereomeric salts formed during the resolution by (S)-(+)-2-benzylaminobutanol was measured and discussed. It was recognized that the (S)-(+)-benzylaminobutanol (S)-(+)-N-formylphenylalanine salt exists in two polymorphic modifications. The effect of structurally related chiral and achiral auxiliary reagents in the above resolution was also studied. Thus, (S)-(+)-2-benzylaminobutanol was applied together with an (R)-(+)-1-phenylethylamine auxiliary resolving agent and benzylamine was used as a half-equivalent achiral basic reagent in a Pope-Peachey type resolution of N-formylphenylalanine by (S)-(+)-2-benzylaminobutanol. The results are compared to those obtained by the structurally related (R)-(+)-1-phenylethylamine chiral auxiliary.
Palovics, Emese,Bereczki, Laura,Marthi, Katalin,Pokol, Gyoergy,Faigl, Ferenc,Fogassy, Elemer
p. 2531 - 2536
(2008/03/15)

An artificial receptor for the intermolecular and enantioselective formation of peptide sheets
Peptide strands coupled at the C terminus to bis[p(aminomethyl)phenyl] ether allow in CHCl3 solution association of lipophilic N-protected peptides with hydrogen bonds in the mode of antiparallel β-sheets; the enantioselectivity observed with a phenylalanine derivative is characterized by a binding constant ratio of around 15.
Eblinger, Frank,Schneider, Hans-Joerg
p. 2297 - 2298
(2007/10/03)

ASYMMETRIC HYDROGENATION IN THE PRESENCE OF BISDIPHENYLPHOSPHINE COMPLEXES OF RHODIUM. 2. 2R-3-PHENYL-2-(N-METHYL-DIPHENYLPHOSPHINAMINO)-1-DIPHENYLPHOSPHINOXYPROPANE(1,5-CYCLOOCTADIENE)RHODIUM(I) PERCHLORATE HYDROGENATION CATALYST
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Pavlov, V. A.,Voloboev, A. A.,Gorshkova, L. S.,Karpeiskaya, E. I.,Klabunovskii, E. I.
p. 464 - 469
(2007/10/02)