A mild and chemoselective method for the reduction of conjugated isoxazolines to beta-hydroxy ketones.

A new procedure for the selective reduction of conjugated Delta(2)-isoxazolines to the corresponding unsaturated beta-hydroxy ketones is described. The use of SmI(2) as the reducing agent and B(OH)(3) to hydrolyze the resulting imine results in a mild, convenient, and chemoselective protocol for this otherwise difficult transformation and complements existing methodology for the preparation of beta-hydroxy ketones via nitrile oxides.