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

共 82 条

[41] Gold(I)-Catalyzed Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes [J].

Lopez-Carrillo, Veronica ;

Echavarren, Antonio M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (27) :9292-9294

[42] Platinum dichloride-catalyzed cycloisomerization of ene-ynamides [J].

Marion, F ;

Coulomb, J ;

Courillon, C ;

Fensterbank, L ;

Malacria, M .

ORGANIC LETTERS, 2004, 6 (09) :1509-1511

[43]

Martín-Matute B, 2001, ANGEW CHEM INT EDIT, V40, P4754, DOI 10.1002/1521-3773(20011217)40:24<4754::AID-ANIE4754>3.0.CO

[44]

2-9

[45] Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2:: The role of platinum carbenes as intermediates [J].

Martín-Matute, B ;

Nevado, C ;

Cárdenas, DJ ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5757-5766

[46] Cyclizations of enynes catalyzed by PtCl2 or other transition metal chlorides:: Divergent reaction pathways [J].

Méndez, M ;

Muñoz, MP ;

Nevado, C ;

Cárdenas, DJ ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10511-10520

[47] Platinum-catalyzed alkoxy- and hydroxycyclization of enynes [J].

Méndez, M ;

Muñoz, MP ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11549-11550

[48] Cycloisomerization of 1,n-enynes:: Challenging metal-catalyzed rearrangements and mechanistic insights [J].

Michelet, Veronique ;

Toullec, Patrick Y. ;

Genet, Jean-Pierre .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4268-4315

[49] Skeletal reorganization of enynes catalyzed by InCl3 [J].

Miyanohana, Y ;

Chatani, N .

ORGANIC LETTERS, 2006, 8 (10) :2155-2158

[50] Skeletal reorganization of enynes into 1-vinylcycloalkenes in ionic liquids [J].

Miyanohana, Y ;

Inoue, H ;

Chatani, N .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8541-8543

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