Synthesis of a Functionalized Allylic Phosphine Oxide

Abstract

A functionalized allylic phosphine oxide has been prepared by regioselective bromination of 2-(methyldiphenylphosphinoyl)-1-propene followed by nucleophilic substitution with acetate. Hydrolysis and protection yielded the target compound.

Notes

Our attempts to use allylic phosphines oxides to prepare dienes such as 1 typically result in E/Z mixtures which are inseparable.

Other attempts which failed to give rearrangement product: (1) decalin, 150°C, sealed tube, 24 h; (2) decane, reflux, 24 h; (3) 5 mol % (Ph₃P)₄Pd, THF, 35 °C 24 h, reflux, 24 h.