SYNTHESIS OF A NOVEL FLUORINE-CONTAINING EFFIСIENT CHIRAL AUXILIARY (S)-N-(2-BENZOILPHENYL)-1-(2-FLUOROBENZYL)PYRROLIDINE-2-CARBOXAMIDE AND ITS N(II) COMPLEX OF SHIFF BASE WITH SERINE

Abstract

New fluorine-containing chiral auxiliary (S)-N-(2-benzoyl-phenyl)-1-(2- fluorobenzyl)pyrolidyne-2-carboxamide ((S)-2-FBPB) and its plane-square Ni(II) complex of Shiff base with serine is synthesized. The synthesis of chiral auxiliary has been carried out in the presence of CH₂Cl₂ at 0 ^oC via condensation of 2-aminobenzophenone with 2-fluorobenzylproline, through intermediate formation of chloranhydride in the presence of PCl₅. The synthesis was carried out in CH₃OH in the presense of strong base (KOH). As expected during the synthesis of the serine complex with new fluorine-containing chiral auxiliary (S)-2-FBPB of diastereoizomeric complexes (S,R)/(S,S) in a ratio 99/1 has been derived.