A detailed study of a procedure for the selective reduction of Delta(2)-isoxazolines to the corresponding beta-hydroxy ketones is reported. The use of iron and ammonium chloride as the reducing agent in the presence of water results in a facile and chemoselective protocol for the preparation of beta-hydroxy ketones, including the conjugated beta-hydroxy ketones.

A novel route to the synthesis of Delta2-isoxazoline derivatives is described. Reaction of beta,gamma-unsaturated oximes with aryl bromides via palladium-catalyzed carboetherification affords 3,5-disubstituted Delta2-isoxazolines in good yields. The use of Xantphos as ligand is crucial for the transformation. The carboetherification products can be further converted to beta-hydroxy ketones in the presence of Fe powder and NH4Cl.

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