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

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