Synthesis of γ-Hydroxy-α,β-unsaturated Esters and Nitriles from Chiral Cyanohydrins

The Horner–Wittig reaction of cyanomethyl- and carbethoxymethyl diphenylphosphine oxides with a range of O-protected chiral α-hydroxy aldehydes is described. The α-hydroxy aldehydes were prepared with high enantiomeric purity from chiral O-protected cyanohydrins. The γ-hydroxy-α,β-unsaturated compounds formed were isolated in high enantiomeric purity and excellent yield. In all cases complete E-selectivity was observed.