Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement

被引：122

作者：

Kirsch, Stefan F. ^{[1
]}

Binder, Joerg T. ^{[1
]}

Crone, Benedikt ^{[1
]}

Duschek, Alexander ^{[1
]}

Haug, Timm T. ^{[1
]}

Liebert, Clemence ^{[1
]}

Menz, Helge ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 13期

关键词：

cyclization; domino reactions; gold; homogeneous catalysis; rearrangement;

D O I：

10.1002/anie.200604544

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Au-spicious! Under silver-free conditions, simple 3-silyloxy-1,5-enynes were converted into complex cyclopentenes by a gold(I)-catalyzed sequence that likely proceeds through a carbocyclization followed by a pinacol rearrangement. For the final demetalation step, isopropyl alcohol and N-iodosuccinimide are effectively utilized, and the resulting products are set up for a wealth of further reactions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2310 / 2313

页数：4

共 69 条

[1]

[Anonymous], 2005, ANGEW CHEM, V117, P7150, DOI DOI 10.1002/ANGE.200502735

[2] Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions [J].

Barluenga, J ;

Diéguez, A ;

Fernández, A ;

Rodríguez, F ;

Fañanás, FJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) :2091-2093

[3]

BARLUENGA J, 2006, ANGEW CHEM, V118, P2145

[4] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC LETTERS, 2006, 8 (20) :4489-4492

[5] Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].

Binder, JT ;

Kirsch, SF .

ORGANIC LETTERS, 2006, 8 (10) :2151-2153

[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] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].

Buzas, A ;

Istrate, F ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (09) :1957-1959

[8] Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].

Buzas, A ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (03) :515-518

[9] Gold(I)-catalyzed formation of 5-methylene-1,3-oxazolidin-2-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

SYNLETT, 2006, (17) :2727-2730

[10] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

← 1 2 3 4 5 6 7 →