The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition

Abstract

Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph₂PO) group, is regiospecific (acetate moves away from the Ph₂PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.