Issue 6, 2000

Regio- and diastereo-selective formation of dicopper(I) and disilver(I) double helicates with chiral 6-substituted 2,2′∶6′,2′′-terpyridines

Abstract

Two enantiomeric pairs of chiral terpy ligands (I and II; III and IV) bearing enantiopure bornyloxy substituents at the 6-position were prepared in high yield, stereoretentive reactions from (1R)-endo- or (1S)-endo-borneol; compounds I, II and III were structurally characterised. Dinuclear double helicates were formed upon reaction with copper(I) salts, but solvent-dependent and reversible formation of mononuclear or dinuclear double-helical complexes was observed with silver(I) salts. The double helicates are formed with good to excellent diastereoselectivity for helical chirality. With these 6-substituted ligands, double helicates can exist as head-to-head (HH ) or head-to-tail (HT ) isomers; in solution, the HT isomers are favored, although solid state interactions can overcome this preference.

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 1999
Accepted
21 Jan 2000
First published
28 Feb 2000

J. Chem. Soc., Dalton Trans., 2000, 945-959

Regio- and diastereo-selective formation of dicopper(I) and disilver(I) double helicates with chiral 6-substituted 2,2′∶6′,2′′-terpyridines

G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, M. Neuburger and M. Zehnder, J. Chem. Soc., Dalton Trans., 2000, 945 DOI: 10.1039/A909158K

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