Cyclobutenes as Isolable Intermediates in the Gold(I)-Catalysed Cycloisomerisation of 1,8-Enynes

被引：65

作者：

Odabachian, Yann ^{[1
]}

Gagosz, Fabien ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, UMR 7652, Organ Synth Lab, F-91128 Palaiseau, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 03期

关键词：

2+2]cycloaddition; cyclobutenes; gold; homogeneous catalysis; PLATINUM-CATALYZED CYCLOISOMERIZATION; GOLD CATALYSIS; ENYNE METATHESIS; REARRANGEMENTS; ARYLALKYNES; 1,3-ENYNES; ACTIVATION; 1,5-ENYNES; MECHANISM; EFFICIENT;

D O I：

10.1002/adsc.200900056

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The gold(I)-catalysed isomerisation of 1,8-enynes allows the efficient synthesis of functionalised bicyclo[5.2.0]nonenes. Notably, these cyclobutenes derivatives can be isolated as reactive intermediates that could undergo subsequent gold(I)-catalysed transformations such as isomerisation, fragmentation or ene reaction to furnish more structurally complex products. This study also provides useful information related to the mechanism leading to metathesis-type derivatives, examples of which were shown to be produced, in the present case, by a gold(I)-catalysed ring fragmentation of the cyclobutene moiety.

引用

页码：379 / 386

页数：8

共 50 条

[1]

[Anonymous], ANGEW CHEM

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3] PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:: Dual role of the Pt catalyst [J].

Bajracharya, GB ;

Nakamura, I ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :892-897

[4] A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES [J].

BLUM, J ;

BEERKRAFT, H ;

BADRIEH, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5567-5569

[5] Gold(I)-Catalyzed [4+2] Annelation/Nucleophilic Addition Sequence: Stereoselective Synthesis of Functionalized Bicyclo[4.3.0]nonenes [J].

Bohringer, Sebastian ;

Gagosz, Fabien .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (16) :2617-2630

[6] Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].

Bruneau, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334

[7]

Buzas A., 2007, Angew. Chem. Int. Ed, V119, P1159

[8] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615

[9] Gold(I)-catalyzed 5-endo hydroxy- and alkoxycyclization of 1,5-enynes:: Efficient access to functionalized cyclopentenes [J].

Buzas, Andrea K. ;

Istrate, Florin M. ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1141-1144

[10] Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3 [J].

Chatani, N ;

Inoue, H ;

Kotsuma, T ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10294-10295

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