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
收藏
页码：2107 / 2110
页数：4
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