Abstract
A racemic planar chiral tertiary amine pCp-CH 2NMe 2 ( HL 1 , pCp = [2.2]paracyclophane-4-yl) was prepared by aminomethylation of the bromide pCp-Br with Eschenmoser’s salt. Direct cyclopalladation of this new ligand with palladium(II) acetate results in the formation of the racemic CN-dimer rac- 3 in a moderate yield of 64%. The enantiomerically pure dimer ( S pl , S pl )- 3 was obtained by the standard procedure of racemic palladacycle resolution using ( S C )-prolinate as a 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 ( S C )-prolinate derivative.
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