Scope of the intramolecular titanocene-catalyzed Pauson-Khand type reaction

被引:113
作者
Hicks, FA [1 ]
Kablaoui, NM [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja990682u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pauson-Khand type conversion of enynes to bicyclic cyclopentenones employing the commercially available precatalyst titanocene dicarbonyl is described. This methodology shows excellent functional group tolerance for a group 4 metallocene-catalyzed process. The scope and limitations of this cyclization with respect to 1,6-, 1,7- and 1,8-enynes with a variety of terminal alkyne substituents, chiral enynes, and enynes containing substituted olefins are described in detail. A mechanism involving carbonylation of an intermediate titanacyclopentene has been proposed.
引用
收藏
页码:5881 / 5898
页数:18
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