The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes

被引：54

作者：

Escribano-Cuesta, Ana ^{[1
]}

Perez-Galan, Patricia ^{[1
]}

Herrero-Gomez, Elena ^{[1
]}

Sekine, Masaki ^{[1
]}

Braga, Ataualpa A. C. ^{[1
]}

Maseras, Feliu ^{[1
,2
]}

Echavarren, Antonio M. ^{[1
,3
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[2] Univ Autonoma, Dept Quim, Bellaterra 08193, Spain

[3] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 30期

关键词：

CATALYZED CYCLOISOMERIZATION REACTIONS; ENYNE METATHESIS; PTCL2-MEDIATED CYCLOISOMERIZATION; POLYFUNCTIONALIZED 1,6-ENYNES; 2+2 CYCLOADDITION; GOLD; PLATINUM; REORGANIZATION; CYCLIZATIONS; ALKYNES;

D O I：

10.1039/c2ob25419k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,6-Enynes with electron-donating substituents at the alkyne undergo gold(I)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale for these effects, and suggest that bicyclo[3.2.0]hept-5-enes are involved as intermediates. We provide the first X-ray structural evidence for the formation of a product of this class in a cycloisomerisation of a 1,6-enyne.

引用

页码：6105 / 6111

页数：7

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