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.