A Practical Titanium-Catalyzed Synthesis of Bicyclic Cyclopentenones and Allylic Amines
The Journal of Organic Chemistry1996Vol. 61(8), pp. 2713–2718
Citations Over TimeTop 10% of 1996 papers
Abstract
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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