Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs

被引:345
作者
Etayo, Pablo [1 ]
Vidal-Ferran, Anton [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, E-43007 Tarragona, Spain
[2] Catalan Inst Res & Adv Studies ICREA, E-08010 Barcelona, Spain
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; ENDOTHELIN RECEPTOR ANTAGONISTS; HIV PROTEASE INHIBITORS; LARGE-SCALE SYNTHESIS; BETA-AMINO ACIDS; KEY INTERMEDIATE; EFFICIENT SYNTHESIS; HOMOGENEOUS HYDROGENATION; HETEROAROMATIC-COMPOUNDS; FUNCTIONALIZED ALKENES;
D O I
10.1039/c2cs35410a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
During the last few decades, rhodium-catalysed asymmetric hydrogenation of diverse alkene classes has emerged as a powerful synthetic tool in the pharmaceutical industry, contributing to the manufacturing of chiral drugs, recent drug candidates for clinical trials, and major synthetic precursors of drugs. Numerous efficient chiral rhodium complexes, most of which are derived from enantiopure phosphorus ligands, have been employed for the preparation of chiral drugs and intermediates thereof. This review article is intended to provide an updated overview of the most striking contributions in this field, organised according to substrate class: acrylate derivatives, itaconate derivatives, alpha-substituted enamides, alpha-arylenol acetates, and minimally functionalised olefins.
引用
收藏
页码:728 / 754
页数:27
相关论文
共 160 条
  • [1] Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine
    Adamczyk, M
    Akireddy, SR
    Reddy, RE
    [J]. ORGANIC LETTERS, 2001, 3 (20) : 3157 - 3159
  • [2] Asymmetric homogeneous hydrogenations at scale
    Ager, David J.
    de Vries, Andre H. M.
    de Vries, Johannes G.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) : 3340 - 3380
  • [3] Synthesis of enantiopure (R)-2-(4-methoxy-3-(3-methoxypropoxy)-benzyl)-3-methylbutanoic acid -: a key intermediate for the preparation of Aliskiren
    Andrushko, Natalia
    Andrushko, Vasyl
    Thyrann, Thomas
    Koenig, Gerd
    Boerner, Armin
    [J]. TETRAHEDRON LETTERS, 2008, 49 (41) : 5980 - 5982
  • [4] Highly Enantioselective Hydrogenation of β-Acyloxy and β-Acylamino α,β-Unsaturated Phosphonates Catalyzed by Rhodium Phosphane-Phosphite Complexes
    Angeles Chavez, M.
    Vargas, Sergio
    Suarez, Andres
    Alvarez, Eleuterio
    Pizzano, Antonio
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2775 - 2794
  • [5] [Anonymous], [No title captured], Patent No. [WO01/64637, 0164637]
  • [6] Clinical efficacy and safety of tolterodine in the treatment of overactive bladder: A pooled analysis
    Appell, RA
    [J]. UROLOGY, 1997, 50 (6A) : 90 - 96
  • [7] Design of molecular catalysts for achievement of high turnover number in homogeneous hydrogenation
    Arai, Noriyoshi
    Ohkuma, Takeshi
    [J]. CHEMICAL RECORD, 2012, 12 (02) : 284 - 289
  • [8] Achiral bis-imine in combination with CoCl2: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol
    Arunkumar, K.
    Reddy, M. Appi
    Kumar, T. Sravan
    Kumar, B. Vijaya
    Chandrasekhar, K. B.
    Kumar, P. Rajender
    Pal, Manojit
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6 : 1174 - 1179
  • [9] Asymmetric synthesis of an MMP-3 inhibitor incorporating a 2-alkyl succinate motif
    Ashcroft, CP
    Challenger, S
    Derrick, AM
    Storey, R
    Thomson, NM
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) : 362 - 368
  • [10] Evaluation of the Dmt-Tic pharmacophore:: Conversion of a potent δ-opioid receptor antagonist into a potent δ agonist and ligands with mixed properties
    Balboni, G
    Guerrini, R
    Salvadori, S
    Bianchi, C
    Rizzi, D
    Bryant, SD
    Lazarus, LH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) : 713 - 720