title: A Practical Titanium-Catalyzed Synthesis of Bicyclic Cyclopentenones and Allylic Amines.
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.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139.
authors.forename: Frederick A.
authors.initials: FA
authors.lastname: Hicks
authors.forename: Scott C.
authors.initials: SC
authors.lastname: Berk
authors.forename: Stephen L.
authors.initials: SL
authors.lastname: Buchwald