(2S,4S)-3-Benzoyl-4-benzyl-2-tert-butyl-1,3-oxazolidin-5-one

In the title compound, C21H23NO3, the central oxazolidinone ring is approximately planar, the maximum deviation from the plane through the central ring being 0.043 (1) Å. The tert-butyl and benzyl substituents are cis to each other and trans to the N-benzoyl group. The interplanar angle between the aromatic rings of the C-benzyl and N-benzoyl groups is 81.10 (4)°

l-Proline-derived ligands to mimic the ‘2-His-1-carboxylate’ triad of the non-haem iron oxidase active site

Non-haem iron(II) oxidases (NHIOs) catalyse a variety of oxidative transformations in biology. The iron-binding environment of the NHIO active site typically incorporates a ‘2-His-1-carboxylate’ facial triad of amino acid side-chains, a motif that has emerged as a defining feature of the enzyme family. Towards the goal of biomimetic, iron-mediated C–H activation we have synthesized a series of peptidomimetic ligands from l-proline. By coupling l-proline to 2,6-bis(bromomethyl)pyridine, 2-(bromomethyl)-6-((tert-butyldimethylsilyloxy)methyl)pyridine and picolinic acid, we have generated several new ligand architectures designed to complex with iron(II) and mimic the NHIO active site. The resulting iron complexes promote modest levels of alkene dihydroxylation and allylic oxidation using hydrogen peroxide as oxidant