Gold(I)-catalyzed [4+2] cycloaddition of N-(hex-5-enynyl) tert-butyloxycarbamates

被引：31

作者：

Buzas, Andrea ^{[1
]}

Istrate, Florin ^{[1
]}

Le Goff, Xavier F. ^{[2
]}

Odabachian, Yann ^{[1
]}

Gagosz, Fabien ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Synth Organ Lab, F-91128 Palaiseau, France

[2] Ecole Polytech, CNRS, Lab Heteroelements & Coordinat, F-91128 Palaiseau, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2009年 / 694卷 / 04期

关键词：

Homogeneous catalysis; Gold complexes; Cycloaddition; Ynamides; GOLD-CATALYZED CYCLOISOMERIZATIONS; RING-CLOSING METATHESIS; HIGHLY EFFICIENT; ALKYNYL BROMIDES; CHIRAL YNAMIDES; N-ALKYNYLATION; PLATINUM; CYCLIZATION; AMIDATIONS;

D O I：

10.1016/j.jorganchem.2008.11.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A study concerning the gold(I)-catalyzed transformation of N-(hex-5-enynyl) tert-butyloxycarbamates is described. The mild conditions employed allow the moderately efficient but stereoselective synthesis of a range of bicyclic carbamates following a formal [4+2] cycloaddition process. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：515 / 519

页数：5

共 46 条

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

Arcadi, Antonio .

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

[2] Gold(I)-catalyzed 5-endo hydroxy- and alkoxycyclization of 1,5-enynes:: Efficient access to functionalized cyclopentenes [J].

Buzas, Andrea K. ;

Istrate, Florin M. ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1141-1144

[3] Synthesis of 3-(arylmethylene)isoindolin-1-ones from ynamides by Heck-Suzuki-Miyaura domino reactions. Application to the synthesis of lennoxamine [J].

Couty, S ;

Liegault, B ;

Meyer, C ;

Cossy, J .

TETRAHEDRON, 2006, 62 (16) :3882-3895

[4] Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730

[5] Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].

Dunetz, JR ;

Danheiser, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777

[6] Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].

Dunetz, JR ;

Danheiser, RL .

ORGANIC LETTERS, 2003, 5 (21) :4011-4014

[7] A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].

Frederick, MO ;

Mulder, JA ;

Tracey, MR ;

Hsung, RP ;

Huang, J ;

Kurtz, KCM ;

Shen, LC ;

Douglas, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369

[8] On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions [J].

Fuerstner, Alois ;

Morency, Louis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5030-5033

[9] Two manifolds for metal-catalyzed intramolecular Diels-Alder reactions of unactivated alkynes [J].

Fuerstner, Alois ;

Stimson, Christopher C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8845-8849

[10] 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

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