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

[11]

O'Mahony DJR, 1998, SYNLETT, P443

[12] An efficient Rh-catalyst system for the intramolecular [4+2] and [5+2] cycloaddition reactions [J].

Wang, B ;

Cao, P ;

Zhang, XM .

TETRAHEDRON LETTERS, 2000, 41 (42) :8041-8044

[13] Three-component cycloadditions: The first transition metal-catalyzed [5+2+1] cycloaddition reactions [J].

Wender, PA ;

Gamber, GG ;

Hubbard, RD ;

Zhang, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2876-2877

[14]

Wender PA, 2001, ANGEW CHEM INT EDIT, V40, P3895, DOI 10.1002/1521-3773(20011015)40:20<3895::AID-ANIE3895>3.0.CO

[15]

2-#

[16] Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5+2] cycloaddition [J].

Wender, PA ;

Bi, FC ;

Brodney, MA ;

Gosselin, F .

ORGANIC LETTERS, 2001, 3 (13) :2105-2108

[17] Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity [J].

Wender, PA ;

Dyckman, AJ .

ORGANIC LETTERS, 1999, 1 (13) :2089-2092

[18] Transition metal-catalyzed [6+2] cycloadditions of 2-vinylcyclobutanones and alkenes: A new reaction for the synthesis of eight-membered rings [J].

Wender, PA ;

Correa, AG ;

Sato, Y ;

Sun, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) :7815-7816

[19] Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5+2] cycloaddition of allenes and vinylcyclopropanes [J].

Wender, PA ;

Zhang, L .

ORGANIC LETTERS, 2000, 2 (15) :2323-2326

[20] The first metal-catalyzed intramolecular [5+2] cycloadditions of vinylcyclopropanes and alkenes: Scope, stereochemistry, and asymmetric catalysis [J].

Wender, PA ;

Husfeld, CO ;

Langkopf, E ;

Love, JA ;

Pleuss, N .

TETRAHEDRON, 1998, 54 (25) :7203-7220