Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcohols

Abstract

Regioselective ring-openings of epoxy alcohols bearing a diphenylphosphinoyl ( Ph₂PO ) group give diols which can undergo stereospecific Horner–Wittig elimination. This method was used to make allylic alcohols, unsaturated β-hydroxy sulfides, homoallylic alcohols and unsaturated amino acids, with control over their absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry.