A planar chiral non-metallocenic analogue of the most popular N,N-dimethylbenzylaminate palladacycle

A racemic planar chiral tertiary amine pCp-CH2NMe2 (HL1, pCp = [2.2]paracyclophane-4-yl) was prepared by aminomethylation of the bromide pCp-Br with Eschenmoser's salt. Cyclopalladation with palladium(II) acetate affords the racemic CN-dimer rac-3. Enantiopure dimer (Spl,Spl)-3 was obtained by racemic palladacycle resolution using (SC)-prolinate as chiral derivatising agent. The ortho-palladated structure, absolute configuration of the chiral plane, and stereochemical peculiarities of the new CN-palladacycle were established by means of NMR spectroscopy and an X-ray diffraction study of its (SC)-prolinate derivative.