Annulation reactions of chromium carbene complexes:: scope, selectivity and recent developments

被引:326
作者
Dötz, KH [1 ]
Tomuschat, P [1 ]
机构
[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
关键词
D O I
10.1039/a801442f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the past three decades Fischer-type carbene complexes have received increasing interest as selective reagents in organic synthesis. Apart from its electron-acceptor properties exploited in carbene ligand centered reactions, the metal carbonyl fragment provides a template for non-classical cycloaddition reactions. The most useful among them is the chromium-mediated benzannulation which allows a one-pot access to densely functionalized oxygenated arenes coordinated to a Cr(CO)(3) fragment. It is compatible with a variety of functional groups, occurs under mild conditions with remarkable chemo-, regio- and diastereoselectivity, and thus has considerable potential in the synthesis of complex targets and natural products.
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页码:187 / 198
页数:12
相关论文
共 41 条
  • [1] THE 1ST BENZANNULATION CHEMISTRY OF MANGANESE CARBENE COMPLEXES - ACTIVATION BY D(0) METALATION
    BALZER, BL
    CAZANOUE, M
    SABAT, M
    FINN, MG
    [J]. ORGANOMETALLICS, 1992, 11 (05) : 1759 - 1761
  • [2] Reaction of Fischer carbene complexes with 1,3-butadiynes: A new strategem for biaryl synthesis with construction of the biaryl bond preceding synthesis of the arenes
    Bao, JM
    Wulff, WD
    Fumo, MJ
    Grant, EB
    Heller, DP
    Whitcomb, MC
    Yeung, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) : 2166 - 2181
  • [3] 3-COMPONENT INTRAMOLECULAR 2-ALKYNE ANNULATIONS OF FISCHER CARBENE COMPLEXES - NEW STRATEGIES FOR STEROID-SYNTHESIS
    BAO, JM
    WULFF, WD
    DRAGISICH, V
    WENGLOWSKY, S
    BALL, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) : 7616 - 7630
  • [4] A DIASTEREOSELECTIVE SYNTHESIS OF AN ARENE CHROMIUMTRICARBONYL COMPLEX VIA A DOTZ REACTION
    BEDDOES, RL
    KING, JD
    QUAYLE, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (17) : 3027 - 3028
  • [5] TOTAL SYNTHESIS OF NATURAL AND ENT-FREDERICAMYCIN-A
    BOGER, DL
    HUTER, O
    MBIYA, K
    ZHANG, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) : 11839 - 11849
  • [6] CONTRASTERIC REGIOCHEMICAL INCORPORATION OF STANNYLACETYLENES IN THE BENZANNULATION REACTION
    CHAMBERLIN, S
    WATERS, ML
    WULFF, WD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 3113 - 3114
  • [7] SOLVENT, CHELATION AND CONCENTRATION EFFECTS ON THE BENZANNULATION REACTION OF CHROMIUM CARBENE COMPLEXES AND ACETYLENES
    CHAN, KS
    PETERSON, GA
    BRANDVOLD, TA
    FARON, KL
    CHALLENER, CA
    HYLDAHL, C
    WULFF, WD
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (1-2) : 9 - 56
  • [8] Dotz K.H., 1983, TRANSITION METAL CAR
  • [9] CARBENE LIGANDS AS ANTHRACYCLINONE SYNTHONS .5. ANTHRACYCLINONE RING-C SYNTHESIS VIA CHELATE CARBENE COMPLEXES
    DOTZ, KH
    POPALL, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1158 - 1160
  • [10] VINYLKETENES .2. STABLE SILYL-SUBSTITUTED VINYLKETENES
    DOTZ, KH
    FUGENKOSTER, B
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (04): : 1449 - 1457