Gold(I)-catalyzed rearrangement of alkynyloxiranes: A mild access to divinyl ketones

被引：62

作者：

Cordonnier, Marie-Caroline ^{[1
]}

Blanc, Aurelien ^{[1
]}

Pale, Patrick ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim, CNRS, Lab Synth React Organ, F-67000 Strasbourg, France

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 08期

关键词：

D O I：

10.1021/ol800219k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acyloxylated divinyl ketones are conveniently formed by a new gold(I)-catalyzed rearrangement of (3-acyloxyprop-1-ynyl)oxiranes.

引用

页码：1569 / 1572

页数：4

共 42 条

[1] Palladium-catalyzed cyclization/allylation of in situ-generated α-hydroxy-[3]-cumulene samarium alkoxides:: synthesis of allylated furans [J].

Aurrecoechea, JM ;

Perez, E .

TETRAHEDRON LETTERS, 2003, 44 (16) :3263-3266

[2] Synthesis of tetrasubstituted furans by sequential SmI2-promoted reduction and Pd-catalyzed cyclization [J].

Aurrecoechea, JM ;

Pérez, E .

TETRAHEDRON LETTERS, 2001, 42 (23) :3839-3841

[3] Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction-elimination and Pd(II)-catalyzed cycloisomerization [J].

Aurrecoechea, JM ;

Pérez, E ;

Solay, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :564-569

[4]

BAGUS PS, 1975, CHEM PHYS LETT, V33, P408, DOI 10.1016/0009-2614(75)85741-1

[5] STEROIDAL C-17 ALLENE ACETATES AND THEIR 17(20)-UNSATURATED C-21 ALDEHYDE DERIVATIVES [J].

BENN, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (08) :3113-&

[6] SILVER MEDIATED ACETYLENIC OXY COPE REARRANGEMENT [J].

BLUTHE, N ;

GORE, J ;

MALACRIA, M .

TETRAHEDRON, 1986, 42 (05) :1333-1344

[7] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615

[8] Gold(I)-Catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes [J].

Dai, Lun-Zhi ;

Qi, Ming-Juan ;

Shi, Yong-Ling ;

Liu, Xu-Guang ;

Shi, Min .

ORGANIC LETTERS, 2007, 9 (16) :3191-3194

[9] Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles [J].

Dudnik, Alexander S. ;

Sromek, Anna W. ;

Rubina, Marina ;

Kim, Joseph T. ;

Kel'in, Alexander V. ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1440-1452

[10] Carene terpenoids by gold-catalyzed cycloisomerization reactions [J].

Fürstner, A ;

Hannen, P .

CHEMICAL COMMUNICATIONS, 2004, (22) :2546-2547

← 1 2 3 4 5 →