An efficient Ir(III) catalyst for the asymmetric transfer hydrogenation of ketones in neat water

被引：56
作者：
Li, Xiaohong
Blacker, John
Houson, Ian
Wu, Xiaofeng
Xiao, Jianliang [1 ]
机构：
[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
[2] NPIL Pharma, Huddersfield HD2 1GA, W Yorkshire, England
来源：
SYNLETT | 2006年 / 08期
关键词：
asymmetric transfer hydrogenation; ketones; water; formate; camphor ligand;
D O I：
10.1055/s-2006.932490
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The chiral M-CsDPEN [M = Ru, Rh, Ir; CsDPEN = (R,R,R)- or (S,S,S)-N-camphorsulfonyl-1,2-diphenylethylenediamine] catalysts have been shown to be efficient for the asymmetric transfer hydrogenation (ATH) of aryl ketones by formate in neat water. Of particular note is the Ir-(R,R,R)-CsDPEN catalyst, which catalyzes the ATH of a wide range of ketones and delivers almost full conversions within a few hours at a S/C ratio of 1000 at 40 degrees C in most cases, with enantioselectivities up to 98% ee.
引用
收藏
页码：1155 / 1160
页数：6
相关论文
共 68 条
  • [51] 2-N
  • [52] Cycloruthenated primary and secondary amines as efficient catalyst precursors for asymmetric transfer hydrogenation
    Sortais, JB
    Ritleng, V
    Voelklin, A
    Holuigue, A
    Smail, H
    Barloy, L
    Sirlin, C
    Verzijl, GKM
    Boogers, JAF
    de Vries, AHM
    de Vries, JG
    Pfeffer, M
    [J]. ORGANIC LETTERS, 2005, 7 (07) : 1247 - 1250
  • [53] Asymmetric transfer hydrogenation of ketones in 2-propanol catalyzed by arsinooxazoline-ruthenium(II) complex
    Tan, DM
    Chan, KS
    [J]. TETRAHEDRON LETTERS, 2005, 46 (03) : 503 - 505
  • [54] In situ formation of ligand and catalyst -: application in ruthenium-catalyzed enantioselective reduction of ketones
    Västilä, P
    Wettergren, J
    Adolfsson, H
    [J]. CHEMICAL COMMUNICATIONS, 2005, (32) : 4039 - 4041
  • [55] Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles
    Wang, F
    Liu, H
    Cun, LF
    Zhu, J
    Deng, JG
    Jiang, YZ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) : 9424 - 9429
  • [56] A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air
    Wu, XF
    Vinci, D
    Ikariya, T
    Xiao, JL
    [J]. CHEMICAL COMMUNICATIONS, 2005, (35) : 4447 - 4449
  • [57] Insight into and practical application of pH-controlled asymmetric transfer hydrogenation of aromatic ketones in water
    Wu, XF
    Li, XG
    King, F
    Xiao, JL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) : 3407 - 3411
  • [58] Accelerated asymmetric transfer hydrogenation of aromatic ketones in water
    Wu, XF
    Li, XG
    Hems, W
    King, F
    Xiao, JL
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (13) : 1818 - 1821
  • [59] Xiao J, 2005, CHIM OGGI, V23, P50
  • [60] Transfer hydrogenation of activated C=C bonds catalyzed by ruthenium amido complexes: Reaction scope, limitation, and enantioselectivity
    Xue, D
    Chen, YC
    Cui, X
    Wang, QW
    Zhu, J
    Deng, JG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3584 - 3591
1234567