Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene

被引:78
作者
Bappert, E [1 ]
Helmchen, G [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
asymmetric catalysis; chiral N-heterocyclic carbenes; chiral P ligands; rhodium; enantioselective hydrogenation;
D O I
10.1055/s-2004-829548
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Complexes of the ligand (S,S)-1-(2-diphenylphosphanyl-naphtalen-1-yl)-3-(2-isopropyl-phenyl)-4,5-diphenyl-imidazolin-2-ylidene, a representative of a new class of chiral ligands, were obtained via a short route starting from (S,S)-1,2-diphenyl-ethylen-1,2-diamine; a Rh-complex was found to promote catalytic hydrogenation of a,p unsaturated esters with up to 99% ee.
引用
收藏
页码:1789 / 1793
页数:5
相关论文
共 46 条
  • [1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition
    Alexakis, A
    Winn, CL
    Guillen, F
    Pytkowicz, J
    Roland, S
    Mangeney, P
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) : 345 - 348
  • [2] Looking for stable carbenes: The difficulty in starting anew
    Arduengo, AJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) : 913 - 921
  • [3] Beck J, 1997, Z NATURFORSCH B, V52, P604
  • [4] Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands
    Bolm, C
    Focken, T
    Raabe, G
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (12) : 1733 - 1746
  • [5] The first planar-chiral stable carbene and its metal complexes
    Bolm, C
    Kesselgruber, M
    Raabe, G
    [J]. ORGANOMETALLICS, 2002, 21 (04) : 707 - 710
  • [6] CESAR V, 2004, ANGEW CHEM, V116, P1036
  • [7] Rhodium and iridium complexes of N-heterocyclic carbenes via transmetalation: Structure and dynamics
    Chianese, AR
    Li, XW
    Janzen, MC
    Faller, JW
    Crabtree, RH
    [J]. ORGANOMETALLICS, 2003, 22 (08) : 1663 - 1667
  • [8] Synthesis, X-ray and solid state NMR studies on silver(I) silanethiolates.: Crystal structure of bis[(triphenylphosphine)-(tri-o-tolylsilanethiolato)silver(I)]-toluene(1/2), [{Ag[SSi(C6H4-Me-o)3](PPh3)}2]•2C6H5Me
    Chojnacki, J
    Becker, B
    Konitz, A
    Potrzebowski, MJ
    Wojnowski, W
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (17): : 3063 - 3068
  • [9] C-H activation with N-heterocyclic carbene complexes of iridium and rhodium
    Danopoulos, AA
    Winston, S
    Hursthouse, MB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (16): : 3090 - 3091
  • [10] Synthesis and structural characterisation of stable pyridine- and phosphine-functionalised N-heterocyclic carbenes
    Danopoulos, AA
    Winston, S
    Gelbrich, T
    Hursthouse, MB
    Tooze, RP
    [J]. CHEMICAL COMMUNICATIONS, 2002, (05) : 482 - 483