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Note | Special issue | Vol 67, No. 1, 2006, pp.375-383
Published online, 14th March, 2005
DOI: 10.3987/COM-05-S(T)3
Chiral Complexation of Multidentate N-Heterocyclic Podand Ligands Bearing Histidyl Moieties

Toshiyuki Moriuchi, Masahito Nishiyama, Kazuhiro Yoshida, and Toshikazu Hirao*

*Department of Applied Chemistry, Graduate School of Science, Osaka University, 2-1 Yamadaoka, Suita, Osaka 560-0871, Japan

Abstract

Preorganized left- and right-handed helical conformations of the chiral pentadentate N-heterocyclic ligands bearing the podand histidyl moieties, N,N’-bis{(S)-(+)-1-methoxycarbonyl-2-(4-imidazoyl)ethyl}-2,6-pyridinedicarboxamide (L-BHisPA) and the D-isomer (D-BHisPA), induce the chiral complexation through spiral coordination of the pentadentate BHisPA to Cu(II) center to give L- and D-BHisPA-Cu(II) as a ∧ and Δ enantiomorph, respectively. Each complex is connected by continuous intermolecular hydrogen bonds in a solid state to form a hydrogen-bonded macrocycle with left- or right-handed windmill-like arrangement, respectively. In the case of the Cu(II) complex (L-HisPA-Cu(II)) with the ligand bearing one histidyl pendant group, {(S)-(+)-1-methoxycarbonyl-2-(4-imidazoyl)ethyl}-2-pyridinecarboxamide (L-HisPA), each molecule is assembled in a solid state by continuous intermolecular hydrogen bonds and π-π interaction.