METHOD OF PRODUCING ENANTIOMERICALLY PURE (S)-AMINO ACIDS ON BASIS OF [(S)-BPB-Gly]Ni(II) COMPLEX, DIRECTLY BONDED WITH FULLERENE CORE THROUGH α-CARBON ATOM IN FORM OF CHIRAL (A) AND (C) 1,4-ADDUCTS OF [60]FULLERENE Russian patent published in 2017 - IPC C07F15/04 C07B53/00 

FIELD: chemistry.

SUBSTANCE: invention relates to a method for stereoselective synthesis of (S)-α-fullerenylglycine, wherein α-carbon atom of an acid is directly bonded with a fullerene core, in form of complex of Ni(II) of type of Schiff base with an auxiliary [(S)-BPB] ligand in form of chiral (^f,tA) and (^f,tC) 1,4-adducts of formula (I). Method includes steps A–E. Step A comprises modifying an initial amino acid by its incorporation in form of a Schiff base into coordination sphere of nickel complex with an auxiliary chiral ligand ((S)-2N-(N'-benzylprolyl)aminobenzophenone) [(S)-BPB-Gly]Ni(II). Step B comprises deprotonation of amino acid fragment of obtained complex. Step C comprises stereoselective reaction of anionic (deprotonated) complex with fullerene to form fullerene carbanion. Step D comprises reaction of fullerene carbanion with an electrophile, such as allyl- or benzyl halide, with formation of diastereomeric mixture of target fullerene (^f,tA) and (^f,tC) 1,4-adducts, containing (S)-α-amino acid fragment, directly bonded with fullerene core through α-carbon atom, in form of Schiff base in coordination sphere of Ni(II). Step E comprises separating and cleaning fullerene-containing adducts by column chromatography on silica gel to obtain a mixture of target fullerene (^f,tA) and (^f,tC) 1,4-adducts, containing (S)-α-amino acid fragment in coordination sphere of Ni(II). Invention also relates to a mixture of diastereomers, consisting of (^f,tA) and (^f,tC) 1,4-adducts, and optically pure (^f,tA) and (^f,tC) adducts.

EFFECT: method enables stereoselective synthesis fullerenylglycine derivative having (S)-configuration of α-amino acid stereocentre.

8 cl, 1 dwg, 6 ex

(I)