Metallocene sulfoxides as precursors of metallocenes with planar chirality

被引：75
作者：
Ferber, Benoit [1 ]
Kagan, Henri B. [1 ]
机构：
[1] Univ Paris 11, ICMMO, CNRS, UMR 8182, F-914055 Orsay, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 4-5期
关键词：
chiral ligands; enantioselective catalysis; ferrocenes; lithiation; planar chirality; sulfoxides;
D O I：
10.1002/adsc.200600639
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The preparation of metallocene sulfoxides and their ortho-diastereoselective functionalization are described. The applications of enantiopure 1,2- and 1,3-disubstituted metallocenes are reviewed, with special emphasis on the preparation of ligands for asymmetric catalysis. The sulfoxide functionality is a useful, traceless, chiral diastereoselective ortho-directing group, as explained in the article. It allows one to synthesize a wide range of enantiopure metallocenes with planar chirality and predictible configuration. Most of the examples are related to the ferrocene area.
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收藏
页码：493 / 507
页数：15
相关论文
共 80 条
  • [11] Bolm C, 1999, SYNTHESIS-STUTTGART, P1251
  • [12] BOLM C, 1999, COMPREHENSIVE ASYMME, V2, P697
  • [13] HIGHLY ENANTIOSELECTIVE OXIDATION OF SULFIDES MEDIATED BY A CHIRAL TITANIUM COMPLEX
    BRUNEL, JM
    DITER, P
    DUETSCH, M
    KAGAN, HB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) : 8086 - 8088
  • [14] 1,2-dibromoferrocenes: synthesis and structure
    Butler, IR
    Drew, MGB
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 1999, 2 (06) : 234 - 237
  • [15] Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes
    Cabrera, S
    Arrayás, RG
    Carretero, JC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3944 - 3947
  • [16] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides
    Cabrera, S
    Arrayás, RG
    Carretero, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) : 16394 - 16395
  • [17] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS
    CARRENO, MC
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1717 - 1760
  • [18] Highly selective Negishi cross-coupling reaction of a zinc-metallated ferrocenyl p-tolyl sulfoxide:: New chiral ferrocene-based quinone ligands
    Cotton, HK
    Huerta, FF
    Bäckvall, JE
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) : 2756 - 2763
  • [19] Biocatalytic procedure for obtaining all four diastereoisomers of 1-(1-hydroxyethyl)-3-ethylferrocene: synthons for chiral 1,3-disubstituted ferrocenes
    D'Antona, N
    Lambusta, D
    Morrone, R
    Nicolosi, G
    Secundo, F
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (24) : 3835 - 3840
  • [20] Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes
    Davies, SG
    Loveridge, T
    Teixeira, MFCC
    Clough, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23): : 3405 - 3412
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