Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

Imine complexes of zirconocene, generated by a β-hydrogen abstraction process, which possess a carbon−carbon multiple bond, undergo inter- or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.