Practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines

被引：43

作者：

Hicks, FA ^{[1
]}

Berk, SC ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 08期

关键词：

D O I：

10.1021/jo951763l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines is described. The process converts enyne substrates to iminocyclopentenes using 10 mol% of the air- and moisture-stable precatalyst Cp(2)TiCl(2) in the presence of n-BuLi and triethylsilyl cyanide. The resulting iminocyclopentenes can be hydrolyzed to cyclopentenones in good yields or reduced to allylic silylamines with Red-Al or DIBALH. Treatment of the crude silylamines with acetyl chloride allows isolation of allylic amides in excellent yields.

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页码：2713 / 2718

页数：6

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