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Issue 7, 2010
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Design and synthesis of a tetradentate ‘3-amine-1-carboxylate’ ligand to mimic the metal binding environment at the non-heme iron(ii) oxidase active site

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Abstract

Non-heme iron(II) oxidases (NHIOs) catalyse a diverse array of oxidative chemistry in Nature. As part of ongoing efforts to realize biomimetic, iron-mediated C–H activation, we report the synthesis of a new ‘three-amine-one-carboxylate’ ligand designed to complex with iron(II) and mimic the NHIO active site. The tetradentate ligand has been prepared as a single enantiomer in nine synthetic steps from N-Cbz-L-alanine, pyridine-2,6-dimethanol and diphenylamine, using Seebach oxazolidinone chemistry to control the stereochemistry. X-Ray crystal structures are reported for two important intermediates, along with variable temperature NMR experiments to probe the hindered interconversion of conformational isomers of several key intermediates, 2,6-disubstituted pyridine derivatives. The target ligand and an N-Cbz-protected precursor were each then complexed with iron(II) and tested for their ability to promote alkene dihydroxylation, using hydrogen peroxide as the oxidant.

Graphical abstract: Design and synthesis of a tetradentate ‘3-amine-1-carboxylate’ ligand to mimic the metal binding environment at the non-heme iron(ii) oxidase active site

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Supplementary files

Article information


Submitted
21 Oct 2009
Accepted
21 Dec 2009
First published
04 Feb 2010

Org. Biomol. Chem., 2010,8, 1666-1673
Article type
Paper

Design and synthesis of a tetradentate ‘3-amine-1-carboxylate’ ligand to mimic the metal binding environment at the non-heme iron(II) oxidase active site

V. J. Dungan, Y. Ortin, H. Mueller-Bunz and P. J. Rutledge, Org. Biomol. Chem., 2010, 8, 1666
DOI: 10.1039/B921934J

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