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Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids
Madeleine
Schultz A C,
Jakov
Kulis B,
Julie
Murison B,
Genevieve W.
Andrews A
A
School of Physical and Chemical Sciences, Queensland University of Technology, Brisbane, Qld 4001, Australia.
B
School of Molecular and Microbial Sciences, University of Queensland, St Lucia, Qld 4072, Australia.
C
Corresponding author. Email: madeleine.schultz@qut.edu.au
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Australian Journal of Chemistry 61(4) 297–302 http://dx.doi.org/10.1071/CH07430
Submitted: 13 December 2007
Accepted: 17 March 2008
Published online: 24 April 2008
Abstract
The synthesis of two new families of amino acid-containing chiral ligands, based on methyliminodiacetic acid and nitrilotriacetic acid cores, has been accomplished using a simple protection, solution-phase amide coupling, and deprotection strategy. The amino acids glycine, leucine, aspartic acid, and phenylalanine were used to demonstrate the versatility of the synthetic route, and that no epimerization occurs. The tridentate ligands bear C3 symmetry, whereas the bidentate ligands have C1 symmetry.
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