Jump to main content
Jump to site search

Issue 6, 2016
Previous Article Next Article

Triflate-functionalized calix[6]arenes as versatile building-blocks: application to the synthesis of an inherently chiral Zn(II) complex

Author affiliations

Abstract

Cavity-based metal complexes can find many applications notably in the fields of catalysis and biomimicry. In this context, it was shown that metal complexes of calix[6]arenes bearing three aza-coordinating arms at the small rim provide excellent structural models of the poly-imidazole sites found in the active site of many metallo-enzymes. All these N-donor ligands were synthesized from the 1,3,5-tris-methoxy-p-tBu-calix[6]arene platform, which presents some limitations in terms of functionalization. Therefore, there is a need for the development of new calix[6]arene-based building-blocks selectively protected at the small rim. Herein we describe the regioselective one step synthesis of two calix[6]arenes decorated with triflate groups, i.e. X6H4Tf22 and X6H3Tf33, from the parent calix[6]arene X6H61. It is shown that the triflate groups can either act as protecting or deactivating groups, allowing the elaboration of sophisticated calixarene-based systems selectively functionalized at the large and/or at the small rim. In addition, X6H3Tf33 is functionalized on the A, B, and D rings and thus gives access to inherently chiral compounds, as demonstrated by the synthesis of a rare example of inherently chiral cavity-based metal complex.

Graphical abstract: Triflate-functionalized calix[6]arenes as versatile building-blocks: application to the synthesis of an inherently chiral Zn(ii) complex

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 Nov 2015, accepted on 05 Jan 2016 and first published on 05 Jan 2016


Article type: Paper
DOI: 10.1039/C5OB02367J
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 1950-1957
  •   Request permissions

    Triflate-functionalized calix[6]arenes as versatile building-blocks: application to the synthesis of an inherently chiral Zn(II) complex

    S. Zahim, R. Lavendomme, O. Reinaud, M. Luhmer, G. Evano and I. Jabin, Org. Biomol. Chem., 2016, 14, 1950
    DOI: 10.1039/C5OB02367J

Search articles by author

Spotlight

Advertisements