Asymmetric transfer hydrogenation of ketonic substrates catalyzed by (η5-C5Me5)MCl complexes (M = Rh and Ir) of (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine

被引：176
作者：
Mashima, K [1 ]
Abe, T [1 ]
Tani, K [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan
来源：
CHEMISTRY LETTERS | 1998年 / 12期
关键词：
D O I：
10.1246/cl.1998.1199
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The rhodium and iridium (eta(5)-C5Me5)MCl complexes (3a: M = Rh; 3b: M = Zr) of (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine were found to be catalyst precursors for asymmetric transfer hydrogenation of acetophenone, 2-acetonaphthone, 1-tetralone, and 1-indanone to give (S)-1-phenylethanol (90% ee), (S)-1-(2-naphthyl)ethanol (85% ee), (s)-1-tetralol (97% ee), and (S)-indanol (99% ee), respectively.
引用
收藏
页码：1199 / 1200
页数：2
相关论文
共 23 条
  • [1] Structure of the diamine-Rh(I) precursor in the asymmetric hydride transfer reduction of ketones: A theoretical and experimental approach
    Bernard, M
    Guiral, V
    Delbecq, F
    Fache, F
    Sautet, P
    Lemaire, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) : 1441 - 1446
  • [2] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture
    Fujii, A
    Hashiguchi, S
    Uematsu, N
    Ikariya, T
    Noyori, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) : 2521 - 2522
  • [3] ASYMMETRIC CATALYTIC REDUCTION OF CARBONYL-COMPOUNDS USING C-2 SYMMETRICAL DIAMINES AS CHIRAL LIGANDS
    GAMEZ, P
    FACHE, F
    LEMAIRE, M
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (03) : 705 - 718
  • [4] RHODIUM-PERFLUOROBENZENETHIOLATO AND IRIDIUM-PERFLUOROBENZENETHIOLATO COMPLEXES, [(C5ME5)IR(SC6F5)2], [(C5ME5)IR(SC6F4H-P)2] AND [(C5ME5)2RH2(MU-SC6F5)3][(C5ME5)RH(SC6F5)3] - SYNTHESES, CRYSTAL-STRUCTURES AND SOLUTION BEHAVIOR
    GARCIA, JJ
    TORRENS, H
    ADAMS, H
    BAILEY, NA
    SHACKLADY, A
    MAITLIS, PM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (10): : 1529 - 1536
  • [5] OPTICALLY-ACTIVE PHENANTHROLINES IN ASYMMETRIC CATALYSIS .3. HIGHLY EFFICIENT ENANTIOSELECTIVE TRANSFER HYDROGENATION OF ACETOPHENONE BY CHIRAL RHODIUM 3-ALKYL PHENANTHROLINE CATALYSTS
    GLADIALI, S
    PINNA, L
    DELOGU, G
    DEMARTIN, S
    ZASSINOVICH, G
    MESTRONI, G
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (09) : 635 - 648
  • [6] Highly stereoselective formation of Cp*IrCl complexes of N,N-dimethylamino acids
    Grotjahn, DB
    Joubran, C
    Hubbard, JL
    [J]. ORGANOMETALLICS, 1996, 15 (04) : 1230 - 1235
  • [7] The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones
    Haack, KJ
    Hashiguchi, S
    Fujii, A
    Ikariya, T
    Noyori, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03): : 285 - 288
  • [8] ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES
    HASHIGUCHI, S
    FUJII, A
    TAKEHARA, J
    IKARIYA, T
    NOYORI, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) : 7562 - 7563
  • [9] Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer
    Hashiguchi, S
    Fujii, A
    Haack, KJ
    Matsumura, K
    Ikariya, T
    Noyori, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) : 288 - 290
  • [10] BUILDING BRIDGES BETWEEN INORGANIC AND ORGANIC-CHEMISTRY (NOBEL LECTURE)
    HOFFMANN, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (10): : 711 - 724
123