A planar chiral non-metallocenic analogue of the most popular N,N-dimethylbenzylaminate palladacycle |
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| Authors: | Valery V. Dunina Eugeniya I. TurubanovaOlga N. Gorunova Michail V. LivantsovKonstantin A. Lyssenko Dmitrii Yu. AntonovYuri K. Grishin |
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| Affiliation: | a Department of Chemistry, M.V. Lomonosov Moscow State University, Lenin Hills, 119991 Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation |
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| Abstract: | 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 (Spl, Spl)-3 was obtained by the standard procedure of racemic palladacycle resolution using (SC)-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 (SC)-prolinate derivative. |
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| Keywords: | Planar chirality Azapalladacycles Enantiomer separation Chirality transfer X-ray study |
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