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

被引:399
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 [J].
Funami, Hideaki ;
Kusama, Hiroyuki ;
Iwasawa, Nobuharu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :909-911
[52]   Carene terpenoids by gold-catalyzed cycloisomerization reactions [J].
Fürstner, A ;
Hannen, P .
CHEMICAL COMMUNICATIONS, 2004, (22) :2546-2547
[53]   Platinum-catalyzed cycloisomerization reactions of enynes [J].
Fürstner, A ;
Stelzer, F ;
Szillat, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) :11863-11869
[54]   Novel rearrangements of enynes catalyzed by PtCl2 [J].
Fürstner, A ;
Szillat, H ;
Stelzer, F .
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 [J].
Fürstner, A ;
Szillat, H ;
Gabor, B ;
Mynott, R .
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 [J].
Gao, Q ;
Zheng, BF ;
Li, JH ;
Yang, D .
ORGANIC LETTERS, 2005, 7 (11) :2185-2188
[57]   Gold(I)-Catalyzed Enantioselective [4+2]-Cycloaddition of Allene-dienes [J].
Gonzalez, Ana Z. ;
Toste, F. Dean .
ORGANIC LETTERS, 2010, 12 (01) :200-203
[58]   Ligand effects in homogeneous Au catalysis [J].
Gorin, David J. ;
Sherry, Benjamin D. ;
Toste, F. Dean .
CHEMICAL REVIEWS, 2008, 108 (08) :3351-3378
[59]   Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes [J].
Gorin, David J. ;
Watson, Iain D. G. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3736-+
[60]   Relativistic effects in homogeneous gold catalysis [J].
Gorin, David J. ;
Toste, F. Dean .
NATURE, 2007, 446 (7134) :395-403