Diastereoselective assembly of chiral RuII-coordinated depsipeptide-dendrimers

Buschhaus B, Hirsch A (2005)


Publication Type: Journal article, Original article

Publication year: 2005

Journal

Original Authors: Buschhaus B., Hirsch A.

Publisher: Wiley-VCH Verlag

Pages Range: 1148-1160

Journal Issue: 6

DOI: 10.1002/ejoc.200400712

Abstract

The synthesis, characterization and chiroptical properties of chiral dendrimers 11-14 formed by ruthenium coordination of 2,2′-bipyridine (bpy*) ligands 4, 7, 8 and 10 involving two pairs of enantiomerically pure depsipeptide dendrons bound in 4,4′-position are described. In the case of the first and second generation ligands 4, 7 and 8 the metallodendrimers 11, 12 and 13 are formed containing a central [Ru(bpy*)] core. After coordination of the third generation dendritic ligand 10 the metallodendrimer 14 with two bpy* ligands, {[Ru(bpy*) -Cl] core) was isolated. The corresponding metallodendrimer 15 with three bpy* ligands was formed in traces only. Dendrimers 11, 12 and 13 are the first chiral metallodendrimers involving an [Ru(bpy*)] core. This chiral coordination motif can have either a A or a A configuration. To elucidate if there is a preference for a certain configuration H NMR and CD spectroscopy and analytical HPLC were applied. It was found that for the first generation dendrimer 11 the corresponding diastereoisomers with A and A configuration are formed in equal amounts. On the other hand the A diastereoisomers of 12 and 13 are preferably formed upon coordination of the second generation dendrons 7 and 8 with all-(R,R) configuration (8) or mixed (S, S)-(R,R) configuration (7). This demonstrates that the configuration of the outer rather than the inner layer within the depsipeptide dendrons determines which isomer is preferably formed. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

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How to cite

APA:

Buschhaus, B., & Hirsch, A. (2005). Diastereoselective assembly of chiral RuII-coordinated depsipeptide-dendrimers. European Journal of Organic Chemistry, 6, 1148-1160. https://dx.doi.org/10.1002/ejoc.200400712

MLA:

Buschhaus, Boris, and Andreas Hirsch. "Diastereoselective assembly of chiral RuII-coordinated depsipeptide-dendrimers." European Journal of Organic Chemistry 6 (2005): 1148-1160.

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