Ni(II)-PPP complexes:: From the hydroamination of activated olefins to the synthesis of β-amino acids

被引:20
作者
Fadini, L [1 ]
Togni, A [1 ]
机构
[1] ETH Honggerberg, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
关键词
activated olefins; beta-amino acids; asymmetric catalysis; hydroamination nickel;
D O I
10.2533/000942904777677939
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Complexes of the type [Ni(PPP)(soIvent)]X-2 containing ferrocenyl tridentate ligands have been prepared and used as catalysts in the asymmetric hydroamination of activated olefins (i.e. bearing an electron-withdrawing group). In the case of acrylonitrile derivatives the addition of aliphatic amines displayed relatively high activities and moderate enantioselectivity (yields up to 99%, ee's up to 69%). The reactions were also carried out in various ionic liquids (imidazolium and picolinium salts) with results comparable to those obtained in common organic solvents. Additionally, we describe the conversion of several products to beta-amino acid derivatives.
引用
收藏
页码:208 / 211
页数:4
相关论文
共 26 条
  • [1] The first tridentate phosphine ligand combining planar, phosphorus and carbon chirality
    Barbaro, P
    Bianchini, C
    Giambastiani, G
    Togni, A
    [J]. CHEMICAL COMMUNICATIONS, 2002, (22) : 2672 - 2673
  • [2] A NEW CHIRAL TRIDENTATE FERROCENYL LIGAND - SYNTHESIS AND CHARACTERIZATION OF ITS PALLADIUM(II) AND NICKEL(II) COMPLEXES
    BARBARO, P
    TOGNI, A
    [J]. ORGANOMETALLICS, 1995, 14 (07) : 3570 - 3573
  • [3] Brunet J.J., 2001, CATALYTIC HETEROFUNC, P91
  • [4] CARDILLO G, 1996, CHEM SOC REV, P117
  • [5] The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination
    Dorta, R
    Egli, P
    Zurcher, F
    Togni, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10857 - 10858
  • [6] Drey C. N., 1985, CHEM BIOCH AMINO ACI, P25
  • [7] Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins
    Fadini, L
    Togni, A
    [J]. CHEMICAL COMMUNICATIONS, 2003, (01) : 30 - 31
  • [8] FADINI L, UNPUB
  • [9] STEREOSELECTION EFFECTS IN THE CATALYTIC HYDROAMINATION CYCLIZATION OF AMINOOLEFINS AT CHIRAL ORGANOLANTHANIDE CENTERS
    GAGNE, MR
    BRARD, L
    CONTICELLO, VP
    GIARDELLO, MA
    STERN, CL
    MARKS, TJ
    [J]. ORGANOMETALLICS, 1992, 11 (06) : 2003 - 2005
  • [10] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES
    HAYASHI, T
    MISE, T
    FUKUSHIMA, M
    KAGOTANI, M
    NAGASHIMA, N
    HAMADA, Y
    MATSUMOTO, A
    KAWAKAMI, S
    KONISHI, M
    YAMAMOTO, K
    KUMADA, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 1138 - 1151