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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.; Walden, Melissa T.; Yufit, Dmitry S.; Desa, Tanya; Lurie-Luke, Elena; Williams, J.A. Gareth

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


Authors

Raminder S. Mulla

Melissa T. Walden

Dmitry S. Yufit

Tanya Desa

Elena Lurie-Luke



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.

Citation

Mulla, R. S., Walden, M. T., Yufit, D. S., Desa, T., Lurie-Luke, E., & Williams, J. G. (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), 6410-6420. https://doi.org/10.1016/j.tet.2017.09.032

Journal Article Type Article
Acceptance Date Sep 15, 2017
Online Publication Date Sep 19, 2017
Publication Date Sep 19, 2017
Deposit Date Oct 20, 2017
Publicly Available Date Sep 13, 2018
Journal Tetrahedron
Print ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 73
Issue 45
Pages 6410-6420
DOI https://doi.org/10.1016/j.tet.2017.09.032

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