Rhodium catalyzed [4+2+2] cycloaddition and alkyne insertion: A new route to eight-membered rings

被引：105

作者：

Gilbertson, SR ^{[1
]}

DeBoef, B ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 30期

关键词：

D O I：

10.1021/ja026536x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel variation of the rhodium catalyzed [4 + 2] reaction is reported. A catalyst system that forms an eight-membered ring product from the incorporation of an alkyne into a dienyne is discussed. The products are formed with high diastereoselectivity and in good yield. The highest yields are obtained with alkynes that possess either an oxygen or nitrogen in the propargyl position. Examples are presented where the tether between the alkyne and the diene contains three or four atoms. Copyright © 2002 American Chemical Society.

引用

收藏

页码：8784 / 8785

页数：2

相关论文

共 28 条

[1] Transition metal-catalyzed [4+2+2] cycloadditions of bicyclo[2.2.1]hepta-2,5-dienes (norbornadienes) and bicyclo[2.2.2]octa-2,5-dienes [J].

Chen, Y ;

Kiattansakul, R ;

Ma, B ;

Snyder, JK .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :6932-6942

[2] Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation Pauson-Khand annulation reactions [J].

Evans, PA ;

Robinson, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4609-4610

[3] Rhodium-catalyzed asymmetric [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS ;

Genov, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10077-10080

[4] Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS .

TETRAHEDRON LETTERS, 1998, 39 (15) :2075-2078

[5] Rhodium(I)-catalyzed asymmetric intramolecular Pauson-Khand-type reaction [J].

Jeong, N ;

Sung, BK ;

Choi, YK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6771-6772

[6] Rhodium(I)-catalyzed intramolecular Pauson-Khand reaction [J].

Jeong, N ;

Lee, S ;

Sung, BK .

ORGANOMETALLICS, 1998, 17 (17) :3642-3644

[7] NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].

JOLLY, RS ;

LUEDTKE, G ;

SHEEHAN, D ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966

[8] The rhodium-catalyzed Pauson-Khand reaction [J].

Kobayashi, T ;

Koga, Y ;

Narasaka, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :73-87

[9]

Koga Y, 1998, CHEM LETT, P249

[10] ON THE ASYMMETRIC RH(I) CATALYZED [4+2] CYCLOISOMERIZATION REACTION - ELECTRONIC AND TORSIONAL LIGAND CONTROL OF ABSOLUTE STEREOSELECTION [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON, 1994, 50 (21) :6145-6154