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Issue 39, 2014
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Terpenols as substituents for the diastereoselective formation of enantiomerically pure triple lithium-bridged helicate type-coordination compounds

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Abstract

The terpenols L(−)-borneol, (1S2S3S5R)-3-pinanol, (−)-menthol, and (−)-myrtenol are easily available chiral alcohols for the preparation of enantiomerically pure catechol esters 1–4-H2. Those ligands are used for the hierarchical assembly of triple lithium-bridged dinuclear titanium(IV) triscatecholate helicates Li[Li3(1–4)6Ti2]. In solution, the dimeric species are in a solvent dependent equilibrium with the monomer Li2[(1–4)3Ti]. The equilibrium is studied by 1H NMR. CD spectroscopy indicates that the configuration at the complex units of the enantiomerically pure dimeric α-chiral derivatives Li[Li3(1–3)6Ti2] is opposite to the configuration of the monomers Li2[(1–3)3Ti]. For the γ-chiral complex Li2[(4)3Ti] only a de of 25% is observed and in this case no interpretation of the mechanism of stereocontrol is possible.

Graphical abstract: Terpenols as substituents for the diastereoselective formation of enantiomerically pure triple lithium-bridged helicate type-coordination compounds

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Publication details

The article was received on 27 May 2014, accepted on 04 Aug 2014 and first published on 06 Aug 2014


Article type: Paper
DOI: 10.1039/C4DT01553C
Citation: Dalton Trans., 2014,43, 14636-14643
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    Terpenols as substituents for the diastereoselective formation of enantiomerically pure triple lithium-bridged helicate type-coordination compounds

    M. Albrecht, E. Isaak, H. Shigemitsu, V. Moha, G. Raabe and R. Fröhlich, Dalton Trans., 2014, 43, 14636
    DOI: 10.1039/C4DT01553C

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