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

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共 38 条

[31] Insights into the origin of high activity and stability of catalysts derived from bulky, electron-rich monophosphinobiaryl ligands in the Pd-catalyzed C-N bond formation [J].

Strieter, ER ;

Blackmond, DG ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :13978-13980

[32] AN UNUSUAL MECHANISM OF A PALLADIUM-CATALYZED INTRAMOLECULAR CARBAMETALATION - A NOVEL PALLADIUM-CATALYZED REARRANGEMENT [J].

TROST, BM ;

TANOURY, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1636-1638

[33] An asymmetric synthesis of the tricyclic core and a formal total synthesis of roseophilin via an enyne metathesis [J].

Trost, BM ;

Doherty, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (16) :3801-3810

[34] A CYCLOADDITION APPROACH TO CYCLOPENTENES VIA METALLADIENES AS 4-PI PARTNERS [J].

TROST, BM ;

HASHMI, ASK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2183-2184

[35] ON THE MECHANISM OF THE TCPC(HFB)-CATALYZED METATHESIS OF 1,6-ENYNE - EVIDENCE FOR ALKYLIDENEPALLADIUM INTERMEDIATES [J].

TROST, BM ;

HASHMI, ASK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1085-1087

[36] MECHANISTIC DICHOTOMIES IN PD CATALYZED ENYNE METATHESIS OF CYCLIC OLEFINS [J].

TROST, BM ;

TROST, MK .

TETRAHEDRON LETTERS, 1991, 32 (30) :3647-3650

[37] A rationally designed universal catalyst for Suzuki-Miyaura coupling processes [J].

Walker, SD ;

Barder, TE ;

Martinelli, JR ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (14) :1871-1876

[38] Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes [J].

Zhang, LM ;

Kozmin, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11806-11807

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