Synthesis of azepines by a gold-catalyzed intermolecular [4+3]-annulation

被引：200

作者：

Shapiro, Nathan D. ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 29期

关键词：

D O I：

10.1021/ja803890t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.

引用

页码：9244 / +

页数：3

共 22 条

[1] Gold-catalyzed addition of carbon nucleophiles to propargyl carboxylates [J].

Amijs, Catelijne H. M. ;

Opez-Carrillo, Veronica ;

Echavarren, Antonio M. .

ORGANIC LETTERS, 2007, 9 (20) :4021-4024

[2] Alkenyl Fischer carbene complexes and alpha,beta-unsaturated imine derivatives: Synthesis of azepines and mechanistic NMR studies [J].

Barluenga, J ;

Tomas, M ;

Ballesteros, A ;

Santamaria, J ;

Carbajo, RJ ;

LopezOrtiz, F ;

GarciaGranda, S ;

Pertierra, P .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (01) :88-97

[3] Unusual [1,2]- and [1,3]-M(CO)5 shifts in Fischer carbene complexes:: [4+3] and [3+3] annulation reactions of furan and pyrrole rings [J].

Barluenga, J ;

Tomás, M ;

Rubio, E ;

López-Pelegrín, JA ;

García-Granda, S ;

Priede, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3065-3071

[4] Golden carousel in catalysis: The cationic gold/propargylic ester cycle [J].

Correa, Andrea ;

Marion, Nicolas ;

Fensterbank, Louis ;

Malacria, Max ;

Nolan, Steven P. ;

Cavallo, Luigi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :718-721

[5] CARBENOID VERSUS VINYLOGOUS REACTIVITY IN RHODIUM(II)-STABILIZED VINYLCARBENOIDS [J].

DAVIES, HML ;

HU, BH ;

SAIKALI, E ;

BRUZINSKI, PR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4535-4541

[6] Alkynes as masked ylides: Gold-catalysed intermolecular reactions of propargylic carboxylates with sulfides [J].

Davies, Paul W. ;

Albrecht, Sebastien J. -C. .

CHEMICAL COMMUNICATIONS, 2008, (02) :238-240

[7] Highly stereoselective syntheses of five- and seven-membered ring heterocycles from ylides generated by catalytic reactions of styryldiazoacetates with aldehydes and imines [J].

Doyle, MP ;

Hu, WH ;

Timmons, DJ .

ORGANIC LETTERS, 2001, 3 (23) :3741-3744

[8] Highly selective catalyst-directed pathways to dihydropyrroles from vinyldiazoacetates and imines [J].

Doyle, MP ;

Yan, M ;

Hu, WH ;

Gronenberg, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) :4692-4693

[9] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[10] Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes [J].

Gorin, David J. ;

Watson, Iain D. G. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3736-+

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