Asymmetric synthesis ofS-alkyl-substituted (R)-cysteinesvia a chiral NiII complex of the Schiff's base of dehydroalanine with (S)-2-N-(N-benzylprolyl)aminobenzophenone View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2000-08

AUTHORS

A. S. Saghiyan, A. V. Geolchanyan, S. M. Djamgaryan, S. M. Vardapetyan, V. I. Tararov, N. A. Kuz'mina, N. S. Ikonnikov, Yu. N. Belokon, M. North

ABSTRACT

An efficient procedure was developed for the asymmetric synthesis ofS-alkyl derivatives of (R)-cysteine by nucleophilic addition of alkanethiols (BunSH, ButSH, ortert-C5H11SH) to the C=C bond of the dehydroalanine fragment in the NiII complex of the Schiff's base of Δ-Ala with (S)-2-N-(N-benzylprolyl)aminobenzophenone [(S)-BPB-Δ-Ala]NiII. 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%. More... »

PAGES

1460-1463

Journal

TITLE

Russian Chemical Bulletin

ISSUE

8

VOLUME

49

Author Affiliations

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02495097

DOI

http://dx.doi.org/10.1007/bf02495097

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1014632036


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