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Stereospecific synthesis of polyfunctionalized carbacephams induced by titanocene(III) chloride
Gema Ruano1, Justo Martiáñez, Manuel Grande
1Departamento de Química Orgánica, Universidad de Salamanca, E-37008 Salamanca, Spain.
The Journal of Organic Chemistry
|March 1, 2003
Abstract:
Enantiomerically pure N-substituted epoxyalkene-2-azetidinones reacted with titanocene monochloride to give stereospecifically polyfunctionalized bicyclic beta-lactams. Four isomeric epoxyaldehydes 2 reacted with TiCp2Cl to give exclusively the respective carbacephams 7 while under the same reaction conditions the epoxyesters 1, which are more hindered for an intramolecular addition, gave the cyclization products 6 (only two isomers) and/or the elimination products 5 (all isomers).