Synthesis of dendritic catalysts and application in asymmetric transfer hydrogenation

被引:86
作者
Chen, YC
Wu, TF
Jiang, L
Deng, JG [1 ]
Liu, H
Zhu, J
Jiang, YZ
机构
[1] Sichuan Univ, W China Sch Pharm, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China
关键词
D O I
10.1021/jo048317v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Frechet-type core-functionalized chiral diamine-based dendritic ligands and hybrid dendritic ligands condensed from polyether wedge and Newkome-type poly(ether-amide) supported multiple ligands were designed and synthesized. The solubility of hybrid dendrimers was found to be finely controlled by the polyether dendron. The catalytic efficiency and recovery use of dendritic ruthenium complexes were compared in the transfer hydrogenation of acetophenone. The core-functionalized dendritic catalysts demonstrated much better recyclability, which verified the stabilizing effects of the bulky polyether wedge on the catalytically active complex. Moreover, the dendritic catalysts were applied in the asymmetric transfer hydrogenation of ketones, enones, imine, and activated olefin, and moderate to excellent enantioselectivitiy was achieved comparable to that of monomeric catalysts.
引用
收藏
页码:1006 / 1010
页数:5
相关论文
共 48 条
  • [1] Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides
    Ahn, KH
    Ham, C
    Kim, SK
    Cho, CW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 7047 - 7048
  • [2] Carbonylation reactions of iodoarenes with PAMAM dendrimer-palladium catalysts immobilized on silica
    Antebi, S
    Arya, P
    Manzer, LE
    Alper, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) : 6623 - 6631
  • [3] Solid-phase catalysis: A biomimetic approach toward ligands on dendritic arms to explore recyclable hydroformylation reactions
    Arya, P
    Panda, G
    Rao, NV
    Alper, H
    Bourque, SC
    Manzer, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) : 2889 - 2890
  • [4] A divergent, solid-phase approach to dendritic ligands on beads. Heterogeneous catalysis for hydroformylation reactions
    Arya, P
    Rao, NV
    Singkhonrat, J
    Alper, H
    Bourque, SC
    Manzer, LE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) : 1881 - 1885
  • [5] Dendritic catalysts and dendrimers in catalysis
    Astruc, D
    Chardac, F
    [J]. CHEMICAL REVIEWS, 2001, 101 (09) : 2991 - 3023
  • [6] Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst
    Bayston, DJ
    Travers, CB
    Polywka, MEC
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (12) : 2015 - 2018
  • [7] Hydroformylation reactions using recyclable rhodium-complexed dendrimers on silica
    Bourque, SC
    Alper, H
    Manzer, LE
    Arya, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) : 956 - 957
  • [8] Hydroformylation reactions with rhodium-complexed dendrimers on silica
    Bourque, SC
    Maltais, F
    Xiao, WJ
    Tardif, O
    Alper, H
    Arya, P
    Manzer, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3035 - 3038
  • [9] Organometallic derivatives of phosphorus-containing dendrimers. Synthesis, properties and applications in catalysis
    Caminade, AM
    Maraval, V
    Laurent, R
    Majoral, JP
    [J]. CURRENT ORGANIC CHEMISTRY, 2002, 6 (08) : 739 - 774
  • [10] Efficient asymmetric transfer hydrogenation of activated olefins catalyzed by ruthenium amido complexes
    Chen, YC
    Xue, D
    Deng, JG
    Cui, X
    Zhu, J
    Jiang, YZ
    [J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1555 - 1558