A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions

被引:398
作者
Shapiro, Nathan D. [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
gold catalysis; enantioselective catalysis; cycloisomerizations; alkynes; allenes; FISCHER CARBENE COMPLEXES; C-H BOND; GOLD(I)-CATALYZED RING EXPANSION; ALPHA-DIAZOCARBONYL COMPOUNDS; TRANSITION-METAL CATALYSIS; WAGNER-MEERWEIN SHIFT; IN-VITRO SELECTION; CONIA-ENE REACTION; CYCLOISOMERIZATION REACTIONS; CYCLOADDITION REACTIONS;
D O I
10.1055/s-0029-1219369
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Approaches to research in organic chemistry are as numerous as the reactions they describe. In this account, we describe our reactivity-based approach. Using our work in the area of gold catalysis as a background, we discuss how a focus on reaction mechanism and reactivity paradigms can lead to the rapid discovery of new synthetic tools.
引用
收藏
页码:675 / 691
页数:17
相关论文
共 203 条
  • [51] Preparation of substituted cyclopentadienes through platinum(II)-catalyzed cyclization of 1,2,4-trienes
    Funami, Hideaki
    Kusama, Hiroyuki
    Iwasawa, Nobuharu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) : 909 - 911
  • [52] Carene terpenoids by gold-catalyzed cycloisomerization reactions
    Fürstner, A
    Hannen, P
    [J]. CHEMICAL COMMUNICATIONS, 2004, (22) : 2546 - 2547
  • [53] Platinum-catalyzed cycloisomerization reactions of enynes
    Fürstner, A
    Stelzer, F
    Szillat, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 11863 - 11869
  • [54] Novel rearrangements of enynes catalyzed by PtCl2
    Fürstner, A
    Szillat, H
    Stelzer, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6785 - 6786
  • [55] Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin
    Fürstner, A
    Szillat, H
    Gabor, B
    Mynott, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) : 8305 - 8314
  • [56] Ni(II)-catalyzed conia-ene reaction of 1,3-dicarbonyl compounds with alkynes
    Gao, Q
    Zheng, BF
    Li, JH
    Yang, D
    [J]. ORGANIC LETTERS, 2005, 7 (11) : 2185 - 2188
  • [57] Gold(I)-Catalyzed Enantioselective [4+2]-Cycloaddition of Allene-dienes
    Gonzalez, Ana Z.
    Toste, F. Dean
    [J]. ORGANIC LETTERS, 2010, 12 (01) : 200 - 203
  • [58] Ligand effects in homogeneous Au catalysis
    Gorin, David J.
    Sherry, Benjamin D.
    Toste, F. Dean
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3351 - 3378
  • [59] Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes
    Gorin, David J.
    Watson, Iain D. G.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) : 3736 - +
  • [60] Relativistic effects in homogeneous gold catalysis
    Gorin, David J.
    Toste, F. Dean
    [J]. NATURE, 2007, 446 (7134) : 395 - 403