Acyl transfer reactions with phosphine oxides: synthesis of E-homoallylic alcohols, cyclopropyl ketones, and γ-hydroxy ketones
Abstract
Esters of 3-hydroxypropylphosphine oxides rearrange in base by O to C acyl (RCO) transfer to give the hydroxy ketones (8). threo-Selective reduction of (8) leads to pure E-homoallylic alcohols whilst C to O acyl (Ph2PO) transfer leads to γ-hydroxy ketones with nucleophilic aqueous base or cyclopropyl ketones with KOBut–HOBut.