CATALYTIC ASYMMETRIC SYNTHESIS OF ESOMEPRAZOLE BY A TITANIUM COMPLEX WITH A HEXA-AZA-TRIPHENOLIC MACROCYCLE LIGAND

被引:9
|
作者
Song, Weiguo [1 ,2 ]
Dong, Liangjun [2 ]
Zhou, Yuhan [2 ,3 ]
Fu, Yongqiang [2 ]
Xu, Wenfang [1 ]
机构
[1] Shandong Univ, Inst Med Chem, Sch Pharmaceut Sci, Jinan 250100, Peoples R China
[2] Shouguang Fukang Pharmaceut Co Ltd, Shouguang 262700, Peoples R China
[3] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian, Peoples R China
关键词
Asymmetric catalysis; chiral macrocycles; enantioselective sulfoxidation; esomeprazole; ACHIRAL-PHASE CHROMATOGRAPHY; PROTON-PUMP INHIBITOR; SELF-DISPROPORTIONATION; LANTHANIDE(III) COMPLEXES; ORGANIC FRAMEWORK; OXIDATION; SULFIDES; ENANTIOMERS; SULFOXIDATION; H2O2;
D O I
10.1080/00397911.2014.952307
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of esomeprazole via catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfide by a titanium complex with a hexa-aza-triphenolic macrocycle ligand is described. Esomeprazole was prepared with 99.6% ee, which meets the high requirement of the European Pharmacopeia on enantiomeric purity.
引用
收藏
页码:70 / 77
页数:8
相关论文
共 50 条
  • [1] Catalytic Asymmetric Synthesis of Atropisomers Featuring an Aza Axis
    Feng, Jia
    Lu, Chuan-Jun
    Liu, Ren-Rong
    ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (18) : 2537 - 2554
  • [2] Bis-bipyridine hexa-aza-macrocycle complexes of zinc(II) and nickel(II) and the catalytic reduction of carbon dioxide
    Canales, J
    Ramirez, J
    Estiu, G
    Costamagna, J
    POLYHEDRON, 2000, 19 (22-23) : 2373 - 2381
  • [3] An efficient procedure for the synthesis of esomeprazole using a titanium complex with two chiral ligands
    Khomenko, T. M.
    Volcho, K. P.
    Komarova, N. I.
    Salakhutdinov, N. F.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (01) : 124 - 127
  • [4] An efficient procedure for the synthesis of Esomeprazole using a titanium complex with two chiral ligands
    T. M. Khomenko
    K. P. Volcho
    N. I. Komarova
    N. F. Salakhutdinov
    Russian Journal of Organic Chemistry, 2008, 44 : 124 - 127
  • [5] SYNTHESIS, CHARACTERIZATION, AND MOLECULAR-STRUCTURE OF A HEXA-AZA-MACROCYCLIC COMPLEX OF LUTETIUM(III)
    BENETOLLO, F
    BOMBIERI, G
    DECOLA, L
    SMAILES, DL
    VALLARINO, LM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 263 - INOR
  • [6] Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines
    Cai, Lingchao
    Zhang, Kui
    Chen, Shuming
    Lepage, Romain J.
    Houk, K. N.
    Krenske, Elizabeth H.
    Kwon, Ohyun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) : 9537 - 9542
  • [7] Synthesis and Characterization of Complex Compounds of Tetra-aza Macrocyclic Ligand
    Panchbhai, Mayura A.
    Paliwal, L. J.
    Bhave, N. S.
    E-JOURNAL OF CHEMISTRY, 2008, 5 : 1048 - 1054
  • [8] Synthesis and structure of the first homoleptic 1-aza-1,3-diene titanium complex:: A tightrope walk between ligand coordination and ligand coupling
    Scholz, J
    Kahlert, S
    Görls, H
    ORGANOMETALLICS, 2004, 23 (07) : 1594 - 1603
  • [9] Catalytic asymmetric reactions in the synthesis of complex drug targets
    Klapars, Artis
    Campos, Kevin R.
    Waldman, Jacob H.
    Chen, Cheng-yi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [10] Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement
    Goodman, C. Guy
    Johnson, Jeffrey S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (46) : 14574 - 14577