Intramolecular [4+2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes

被引：493

作者：

Nieto-Oberhuber, C

López, S

Echavarren, AM ^{[1
]}

机构：

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

[2] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 17期

关键词：

D O I：

10.1021/ja042257t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New Au(I) complexes with bulky, biphenyl phosphines are the most reactive catalysts for the cyclizations of enynes. 1,6-Enynes with an aryl ring at the alkyne give 2,3,9,9a-tetrahydro-1H-cyclopenta[b]naphthalenes by a 5-exo-dig cyclization followed by a Nazarov-type ring expansion. 1,8-Dien-3-ynes also cyclize by a 5-exo-dig pathway to form hydrindanes. Copyright © 2005 American Chemical Society.

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页码：6178 / 6179

页数：2

相关论文

共 38 条

[1] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[2] 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

[3] REACTIONS OF TRIMERIC 1-BENZYL-2-GOLD(I)IMIDAZOLE LEADING TO AUI CARBENE COMPLEXES - CRYSTAL-STRUCTURE OF [1-BENZYL-3-BENZOYL-IMIDAZOLIN-2-YLIDEN]CHLOROGOLD(I) [J].

BOVIO, B ;

BURINI, A ;

PIETRONI, BR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 452 (1-2) :287-291

[4] PALLADIUM CATALYZED [2+2+2]-CYCLOADDITION REACTIONS VIA CARBOPALLADATION OF 1,6-ENYNES [J].

BROWN, S ;

CLARKSON, S ;

GRIGG, R ;

SRIDHARAN, V .

TETRAHEDRON LETTERS, 1993, 34 (01) :157-160

[5] Strained cyclic cumulene intermediates in Diels-Alder cycloadditions of enynes and diynes [J].

Burrell, RC ;

Daoust, KJ ;

Bradley, AZ ;

DiRico, KJ ;

Johnson, RP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4218-4219

[6] 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

[7] PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes [J].

Chatani, N ;

Furukawa, N ;

Sakurai, H ;

Murai, S .

ORGANOMETALLICS, 1996, 15 (03) :901-903

[8] HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2) [J].

CHATANI, N ;

MORIMOTO, T ;

MUTO, T ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6049-6050

[9] Iridium(I)-catalyzed cycloisomerization of enynes [J].

Chatani, N ;

Inoue, H ;

Morimoto, T ;

Muto, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4433-4436

[10]

Coudanne I, 1998, SYNLETT, P998

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