Oxazoline

These applications include use as ligands in asymmetric catalysis, as protecting groups for carboxylic acids and increasingly as monomers for the production of polymers.

The synthesis of 2-oxazoline rings is well established and in general proceeds via the cyclisation of a 2-amino alcohol (typically obtained by the reduction of an amino acid) with a suitable functional group.

[12] This method proceeds under relatively mild conditions, however, owing to the large amounts of triphenylphosphine oxide produced, is not ideal for large-scale reactions.

The cyclisation of an amino alcohol and an aldehyde produces an intermediate oxazolidine which can be converted to an oxazoline by treatment with a halogen-based oxidising agent (e.g. NBS,[13] or iodine[14]); this potentially proceeds via an imidoyl halide.

The use of catalytic amounts of ZnCl2 to generate oxazolines from nitriles was first described by Witte and Seeliger,[15][16] and further developed by Bolm et al.[17] The reaction requires high temperatures to succeed and is typically performed in refluxing chlorobenzene under anhydrous conditions.

[20][21] Ligands containing a chiral 2-oxazoline ring are used in asymmetric catalysis due to their facile synthesis, wide range of forms and effectiveness for many types of catalytic transformation.

2‑oxazoline, 3‑oxazoline, and 4‑oxazoline (from left to right)