New versatile optically active bipyridines as building blocks for helicating and caging ligands

Hayoz, Pascal; Zelewsky, Alex von

doi:10.1016/s0040-4039(00)79123-4

Cited by 139 publications

(103 citation statements)

References 10 publications

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“…Unless otherwise stated, commercial grade reagents were used without further purification. The following materials were prepared according to literature procedures: 4,5-pineno-2,2'-bipyridine (1) [9] , 2-(2'-iodoethoxy)ethyl-2''-tetrahydro-2H-pyran ether [14] , 1,3,5-tris-bromomethyl-benzene (2) [15] and Ru(DMSO) 4 Cl 2 [16] .…”

Section: Methodsmentioning

confidence: 99%

“…The preparation of 1 was previously described [9,19] where the key step is a Kröhnke-type reaction. [20][21][22] The chiral pinene-type framework of 1 is deprotonated regioselectively by LDA.…”

Section: Methodsmentioning

confidence: 99%

“…[3] C 3 symmetric ligands have been used before for stereoselective syntheses of octahedral metal complexes. [4][5][6][7][8] Since the introduction of "chiralized" pyridine ligands [9] a large number of stereoselective syntheses with various members of this class of chelates has been carried out. [10] Most of these ligands comprise bipyridine moieties.…”

Section: Introductionmentioning

confidence: 99%

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Diastereoselective synthesis of coordination compounds: a chiral tripodal ligand based on bipyridine units and its ruthenium(ii) and iron(ii) complexes

et al. 2004

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Diastereoselective synthesis of coordination compounds: a chiral tripodal ligand based on bipyridine units and its ruthenium(ii) and iron(ii) complexes

et al. 2004

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“…Introduced in 1992 as bidentate ligands for diastereoselective synthesis of mononuclear d metal complexes [1], the 5,6 and 4,5 pinene bipyridine building blocks ( Fig. 1) and their derivatives, have seen a rapid development [2].…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of Ag(I) helicates with new enantiopure 5,6-Chiragen type ligands

Mamula

Bark

Quinodoz

et al. 2018

Inorganica Chimica Acta

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Two new chiral bis-bidentate, C2-symmetrical ligands belonging to the Chiragen family have been synthesised and characterised. They are designed for polynuclear self-assemblies since the two (À)-5,6-pinenebipyridines units are connected by bridges whose length and rigidity avoids the coordination of the bipyridine moieties to the same metal centre. The ligand L1 with a 1,4-dimethylene naphthalene bridge leads, by complexation with Ag(I) cations, to a polymeric, single stranded helix. The helical pitch contains five metal centers, two consecutive metal centers being connected by a bis-bidentate, helically wrapped ligand, one up and the other down resulting in a coordination number four. The chirality (K) around each metal centre is controlled by the six asymmetric carbons of the ligands and the homochirality of the metal centers gives rise to a P orientation at the helix level. The 1 H-NMR measurements of these species in solution indicate a temperature dependent behaviour pointing out possible equilibria between various [Ag n L n ] n+ fragments as confirmed by MS-spectroscopy. The ligand L2 with a 4,4 0 -dimethylene-1,1 0 -biphenyl bridge reacts with Ag(I) and lead to well resolved and temperature independent 1 H-NMR spectra suggesting the formation of a circular helicate.

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“…[18] Figure 3 1 represents a ligand where two 2,2'-bipyridine units are connected through a m-phenylene bridge. Its synthesis was reported recently [17] .…”

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confidence: 99%

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot

et al. 2004

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Tying nice neat knots is demonstrated on a molecular level with the stereoselective synthesis of a trefoil knot. The key reaction was the completely stereoselective formation of a double‐stranded helical precursor from two pinene–bipyridine threads around two CuI centers (the pinene moieties contain stereogenic centers). The helix was then transformed through several steps into 1; demetallation of the complex 1 yielded the configurationally predetermined free trefoil knot.

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New versatile optically active bipyridines as building blocks for helicating and caging ligands

Cited by 139 publications

References 10 publications

Diastereoselective synthesis of coordination compounds: a chiral tripodal ligand based on bipyridine units and its ruthenium(ii) and iron(ii) complexes

Diastereoselective synthesis of coordination compounds: a chiral tripodal ligand based on bipyridine units and its ruthenium(ii) and iron(ii) complexes

Self-assembly of Ag(I) helicates with new enantiopure 5,6-Chiragen type ligands

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot

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