Gold-Catalyzed Tandem Cyclizations of 1,6-Diynes Triggered by Internal N- and O-Nucleophiles

被引：57

作者：

Sperger, Christian A. ^{[1
]}

Fiksdahl, Anne ^{[1
]}

机构：

[1] Norwegian Univ Sci & Technol, Dept Chem, N-7491 Trondheim, Norway

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 13期

关键词：

ALKYLIDENE; CYCLOISOMERIZATIONS; CYCLOADDITIONS; ALKYNES; ACCESS; ACIDS;

D O I：

10.1021/jo100712d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigations on gold-catalyzed tandem cyclization reactions of 1,6-diynes, tethered to nucleophilic functionalities such as amine, carboxylic acid, amide, and sulfonamide, are reported. The ability of such substrates to undergo tandem cyclization, triggered by internal nucleophiles, has been examined. Depending on the substrate, the catalytic system, and reaction conditions, different regioisomers of monocyclic and bridged bicyclic products were obtained.

引用

页码：4542 / 4553

页数：12

共 34 条

[1] Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions [J].

Aelterman, W ;

De Kimpe, N ;

Tyvorskii, V ;

Kulinkovich, O .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :53-58

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3] DOES FORMAL INTRAMOLECULAR TRANSFER OF AN ACIDIC DEUTERIUM TO A SITE OF HALOGEN LITHIUM EXCHANGE SHOW THAT LITHIUM HALOGEN EXCHANGE IS FASTER THAN LOSS OF THE ACIDIC DEUTERIUM - EVIDENCE IN FAVOR OF AN ALTERNATIVE MECHANISM [J].

BEAK, P ;

MUSICK, TJ ;

CHEN, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3538-3542

[4] Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis [J].

Binder, Jorg T. ;

Crone, Benedikt ;

Haug, Timm T. ;

Menz, Helge ;

Kirsch, Stefan F. .

ORGANIC LETTERS, 2008, 10 (05) :1025-1028

[5] TRANSITION-METAL-CATALYZED CYCLIZATION OF ALKYNOIC ACIDS TO ALKYLIDENE LACTONES [J].

CHAN, DMT ;

MARDER, TB ;

MILSTEIN, D ;

TAYLOR, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6385-6388

[6] Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold [J].

Ferrer, Catalina ;

Amijs, Catelijne H. M. ;

Echavarren, Antonio M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1358-1373

[7] Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].

Fuerstner, Alois .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221

[8] The effect of coordination on the reaction of N-tosyl imines with diethylzinc [J].

Gao, FF ;

Deng, MZ ;

Qian, CT .

TETRAHEDRON, 2005, 61 (52) :12238-12243

[9] Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids:: An entry to functionalized γ-lactones [J].

Genin, E ;

Toullec, PY ;

Antoniotti, S ;

Brancour, C ;

Genêt, JP ;

Michelet, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) :3112-3113

[10] Gold catalysis in organic synthesis:: efficient intramolecular cyclization of γ-acetylenic carboxylic acids to 5-exo-alkylidene-butyrolactones [J].

Genin, Emilie ;

Toullec, Patrick Y. ;

Marie, Peggy ;

Antoniotti, Sylvain ;

Brancour, Celia ;

Genet, Jean-Pierre ;

Michelet, Veronique .

ARKIVOC, 2007, :67-78

← 1 2 3 4 →