Russian Chemical Bulletin p. 1460 - 1463 (2000)
Update date:2022-08-10
Topics:
Saghiyan
Geolchanyan
Djamgaryan
Vardapetyan
Tararov
Kuz'mina
Ikonnikov
Belokon'
North
An efficient procedure was developed for the asymmetric synthesis of S-alkyl derivatives of (R)-cysteine by nucleophilic addition of alkanethiols (BunSH, ButSH, or tert-C5H11SH) to the C=C bond of the dehydroalanine fragment in the Ni11 complex of the Schiff's base of Δ-Ala with (S)-2-N-(N-benzylprolyl)aminobenzophenone [(S)-BPB-Δ-Ala]Ni11. Under conditions of thermodynamic control of the reaction, the diastereomeric excess of the complexes with the (S,R)-configuration was 88 - 96%. After decomposition of the complexes, (R)-S-butylcysteine, (R)-S-tert-butylcysteine, and (R)-S-tert-pentylcysteine were isolated with an enantiomeric purity of >97%.
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