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Strategies for the synthesis of HBGl3, a glutamic acid derived ligand bearing phenolic and azacarboxylate donor groups at the nitrogen atom.

Mulla, Raminder S. and Walden, Melissa T. and Yufit, Dmitry S. and Desa, Tanya and Lurie-Luke, Elena and Williams, J.A. Gareth (2017) 'Strategies for the synthesis of HBGl3, a glutamic acid derived ligand bearing phenolic and azacarboxylate donor groups at the nitrogen atom.', Tetrahedron., 73 (45). pp. 6410-6420.

Abstract

The development of a route applicable to the preparation of acyclic glutamic acid-based chelating ligands bearing two different auxiliary donor groups linked to the nitrogen atom by methylene spacers is described and applied to the synthesis of the new polydentate ligand HBGl3, the first example of such a structure. The synthesis is accomplished using a strategy employing reductive amination and t-butyl ester protected intermediates. The most basic pKa values for the HBGl3 ligand have been estimated via potentiometric and UV–Visible titration techniques.

Item Type:Article
Full text:(AM) Accepted Manuscript
Available under License - Creative Commons Attribution Non-commercial No Derivatives.
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1016/j.tet.2017.09.032
Publisher statement:© 2017 This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Date accepted:15 September 2017
Date deposited:20 October 2017
Date of first online publication:19 September 2017
Date first made open access:19 September 2018

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