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

作者：Dunina Valery V^*; Turubanova Eugeniya I; Gorunova Olga N; Livantsov Michail V; Lyssenko Konstantin A; Antonov Dmitrii Yu; Grishin Yuri K

来源：Polyhedron, 2012, 31(1): 413-421.

DOI：10.1016/j.poly.2011.09.043

• Planar chirality
• Azapalladacycles
• Enantiomer separation
• Chirality transfer
• X-ray study

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. 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-pt, S-pt)-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.

• 出版日期2012-1-4