Gold-Catalyzed Rearrangements: Reaction Pathways Using 1-Alkenyl-2-alkynylcyclopropane Substrates

被引：36

作者：

Barluenga, Jose ^{[1
]}

Tudela, Eva ^{[1
]}

Vicente, Ruben ^{[1
]}

Ballesteros, Alfredo ^{[1
]}

Tomas, Miguel ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33006 Oviedo, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 09期

关键词：

alkynes; cyclopropanes; gold; rearrangement; ring expansion; RING EXPANSIONS; CYCLOISOMERIZATION; CYCLIZATION; PLATINUM; ALKYNYLCYCLOPROPANES; ACTIVATION; 1,5-ENYNES; ENYNES;

D O I：

10.1002/anie.201007795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New reactivity patterns: Gold(I) catalyzes the conversion of cyclopentenes (1/1′) into cyclohexadienes (2/3). This profound skeleton rearrangement comprises ring expansion and a [1,2]-alkynyl shift, and is thought to be initiated by the cleavage of the bridging Ci-C bond. The proposed allyl-gold cation intermediate is trapped with alcohols to provide bicyclo[3.2.1]octadiene and tricyclo[3.2.1.02,7]octane derivatives. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2107 / 2110

页数：4

共 46 条

[11] Relativistic effects in homogeneous gold catalysis [J].

Gorin, David J. ;

Toste, F. Dean .

NATURE, 2007, 446 (7134) :395-403

[12]

Hashmi A.S. K., 2010, ANGEW CHEM, V122, P5360, DOI DOI 10.1002/ANGE.200907078

[13]

Hashmi A.S. K., 2005, ANGEW CHEM, V117, P7150, DOI DOI 10.1002/ANGE.200502735

[14] Gold-catalyzed organic reactions [J].

Hashmi, A. Stephen K. .

CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211

[15] Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates [J].

Hashmi, A. Stephen K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5232-5241

[16] The catalysis gold rush: New claims [J].

Hashmi, ASK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (43) :6990-6993

[17] Highly selective gold-catalyzed arene synthesis [J].

Hashmi, ASK ;

Frost, TM ;

Bats, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11553-11554

[18] Formation of Beyerene, Kaurene, Trachylobane, and Atiserene Diterpenes by Rearrangements That Avoid Secondary Carbocations [J].

Hong, Young J. ;

Tantillo, Dean J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5375-5386

[19] Gold-catalyzed cycloisomerizations of enynes:: A mechanistic perspective [J].

Jimenez-Nunez, Eloisa ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2008, 108 (08) :3326-3350

[20]

JOULE JA, 2000, HETEROCYCLIC CHEM, P252

← 1 2 3 4 5 →