Asymmetric synthesis of (R)-S-(1,2,4-triazol-3-yl)cysteines by nucleophilic addition of triazolethiols to a NiII complex with a chiral dehydroalanine Schiff base View Full Text


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Article Info

DATE

2004-04

AUTHORS

A. S. Saghiyan, A. V. Geolchanyan, L. L. Manasyan, G. M. Mkrtchyan, N. R. Martirosyan, S. A. Dadayan, T. V. Kochickyan, V. S. Harutyunyan, A. A. Avetisyan, V. I. Tararov, V. I. Maleev, Yu. N. Belokon'

ABSTRACT

An efficient method was developed for the asymmetric synthesis of (R)-S-(1,2,4-triazol-3-yl)cysteines by the addition of 3,4-disubstituted 1,2,4-triazole-5-thiols at the electrophilic C=C bond in a NiII complex of a Schiff base of dehydroalanine with (S)-N-(N-benzylprolyl)aminobenzophenone. The stereoselectivity of the formation of diastereomeric complexes with the (S,R) configuration under conditions of thermodynamic control of the nucleophilic addition exceeds 94%. Acid treatment of the reaction mixtures afforded enantiomerically pure (R)-S-hetarylcysteines (ee >98%). More... »

PAGES

932-935

References to SciGraph publications

  • 1978. Microbial Production of Essential Amino Acids with Corynebacterium Glutamicum Mutants in NUTRITIONAL IMPROVEMENT OF FOOD AND FEED PROTEINS
  • Identifiers

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    http://scigraph.springernature.com/pub.10.1023/b:rucb.0000037866.13065.c7

    DOI

    http://dx.doi.org/10.1023/b:rucb.0000037866.13065.c7

    DIMENSIONS

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