Solvent-dependent chemoselectivities in additions of beta-carbonyl imines to allyltrimethylsilane with CTAN.
The oxidative coupling of beta-carbonyl imines and allyltrimethylsilane with CTAN were investigated in CH(3)CN and CH(2)Cl(2). In CH(3)CN allylation products were obtained predominantly, while in CH(2)Cl(2), dihydropyrrole products were obtained exclusively. Solvent-assisted nucleophilic cleavage of the intermediate beta-silyl cation is proposed to play a role in the solvent-dependent chemoselectivity.