(pi)-Allyl Palladium Complexes as Efficient and Powerful Alternative for Nucleophilic Substitution on Bicyclo[3.1.0]hexane Sulfonates: Regio-, Chemo- and Stereoselectivity

The preparation of cyclopropylidene bicyclo[3.1.0]hexane derivatives has been performed on both exo- and endo-bicyclo[3.1.0]hexane sulfonates, through nucleophilic substitution via (pi)-allyl palladium complexes. While the endo- and exo-configurations do not particularly affect the selectivities of the products, on the other hand, the ‘hard’ or ‘soft’ nature of nucleophiles dramatically enhances the conservation or not of the integrity of the cyclopropane rings.