caa a22 4500 475761057 CHVBK 20180406123551.0 cr unu---uuuuu 170329e20000801xx s 000 0 eng 10.1007/BF02495097 doi (NATIONALLICENCE)springer-10.1007/BF02495097 Asymmetric synthesis of S -alkyl-substituted ( R )-cysteines via a chiral NiII complex of the Schiff's base of dehydroalanine with ( S )-2- N -( N -benzylprolyl)aminobenzophenone [Elektronische Daten] [A. Saghiyan, A. Geolchanyan, S. Djamgaryan, S. Vardapetyan, V. Tararov, N. Kuz'mina, N. Ikonnikov, Yu. Belokon, M. North] 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%. Kluwer Academic/Plenum Publishers, 2000 dehydroalanine nationallicence thiols nationallicence addition nationallicence diastereoselectivity nationallicence S -alkylcysteines nationallicence asymmetric synthesis nationallicence Saghiyan A. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut Geolchanyan A. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut Djamgaryan S. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut Vardapetyan S. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut Tararov V. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Kuz'mina N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Ikonnikov N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Belokon Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut North M. Department of Chemistry, London Kings College, Strand, WC2R 2LS, London, UK aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/8(2000-08-01), 1460-1463 1066-5285 49:8<1460 2000 49 11172 https://doi.org/10.1007/BF02495097 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495097 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Saghiyan A. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut NATIONALLICENCE 700 1- Geolchanyan A. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut NATIONALLICENCE 700 1- Djamgaryan S. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut NATIONALLICENCE 700 1- Vardapetyan S. Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056, Erevan, Republic of Armenia aut NATIONALLICENCE 700 1- Tararov V. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Kuz'mina N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Ikonnikov N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Belokon Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- North M. Department of Chemistry, London Kings College, Strand, WC2R 2LS, London, UK aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/8(2000-08-01), 1460-1463 1066-5285 49:8<1460 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer