A new class of oxazoline ligands, named SupraBox, was studied. These ligands possess an additional urea functionality to generate supramolecular bidentate ligands in transition-metal complexes, by the establishment of hydrogen bonds between the urea N-hydrogens of one ligand and the carbonyl oxygen of a second one. A library of 16 SupraBox ligands was prepared using 5 differently substituted oxazoline nuclei, 4 linkers and 3 different urea substituents. The formation of copper(II) and palladium(II) complexes was investigated by MS, UV/Vis and 1H-NMR spectroscopy. The SupraBox library was screened in the copper-catalyzed asymmetric benzoylation of vic-diols. Good selectivities were obtained in the kinetic resolution of racemic hydrobenzoin [up to 86 % ee and selectivity (s) = 28] and in the desymmetrization of meso-hydrobenzoin (up to 88 % ee).

SupraBox: chiral supramolecular oxazoline ligands / M. Durini, E. Russotto, L.L. Pignataro, O. Reiser, U. Piarulli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2012:28(2012 Jul), pp. 5451-5461. [10.1002/ejoc.201200516]

SupraBox: chiral supramolecular oxazoline ligands

L.L. Pignataro;
2012

Abstract

A new class of oxazoline ligands, named SupraBox, was studied. These ligands possess an additional urea functionality to generate supramolecular bidentate ligands in transition-metal complexes, by the establishment of hydrogen bonds between the urea N-hydrogens of one ligand and the carbonyl oxygen of a second one. A library of 16 SupraBox ligands was prepared using 5 differently substituted oxazoline nuclei, 4 linkers and 3 different urea substituents. The formation of copper(II) and palladium(II) complexes was investigated by MS, UV/Vis and 1H-NMR spectroscopy. The SupraBox library was screened in the copper-catalyzed asymmetric benzoylation of vic-diols. Good selectivities were obtained in the kinetic resolution of racemic hydrobenzoin [up to 86 % ee and selectivity (s) = 28] and in the desymmetrization of meso-hydrobenzoin (up to 88 % ee).
Acylation; Asymmetric catalysis; N ligands; Self-assembly; Supramolecular chemistry
Settore CHIM/06 - Chimica Organica
lug-2012
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/214729
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