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%).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. I. Chipens, V. A. Slavinskaya, D. E. Sile, D. P. Kreile, E. Kh. Korchagova, and A. K. Strautinya, Izv. Akad. Nauk Latv. SSR, Ser. Khim.[Bull. Acad. Sci. Latv. SSR, Div. Chem. Sci.)], 1985, 259 (in Russian).
T. Toshima, S. Nomoto, T. Wakamiya, and T. Shiba, J. Antibiot., 1976, 27, 1076.
U. Schmidt and E. Oler, Angew. Chem., Int. Ed. Engl., 1976, 15, 42.
M. R. Bovarnik, J. Biol. Chem., 1943, 148, 151.
K. Nakayama, K. Araki, and H. Kase, Adv. Exp. Med. Biol., 1978, 105, 649.
A. Guna, A. K. Mishra, and G. Nanda, Trans. Rose. Res. Inst., 1992, 45, 57.
J. B. Lambertine, A. W. Coulier, and P. Talalay, Mol. Pharmacol., 1970, 6, 481.
Yu. N. Belokon', S. M. Djamgaryan, A. S. Saghiyan, A. S. Ivanov, and V. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 1618 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 1434 (Engl. Transl.)].
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', and M. North, Izv. Akad. Nauk, Ser. Khim., 2000, 1467 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1460].
Yu. N. Belokon', A. S. Saghiyan, S. M. Djamgaryan, V. I. Bakhmutov, and V. M. Belikov, Tetrahedron, 1988, 44, 5507.
V. S. Harutyunyan, T. V. Kochickyan, E. V. Harutyunyan, and A. A. Avetisyan, Khim. Zh. Arm.[Arm. Chem. J.], 2002, 55, 72.
T. V. Kochickyan, E. V. Harutyunyan, V. S. Harutyunyan, and A. A. Avetisyan, Zh. Org. Khim., 2002, 38, 411 [Russ. J. Org. Chem., 2002, 38(Engl. Transl.)].
M. Walter and L. Ramaley, Analyt. Chem., 1973, 45, 307.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Saghiyan, A.S., Geolchanyan, A.V., Manasyan, L.L. et al. 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. Russian Chemical Bulletin 53, 932–935 (2004). https://doi.org/10.1023/B:RUCB.0000037866.13065.c7
Issue Date:
DOI: https://doi.org/10.1023/B:RUCB.0000037866.13065.c7