Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethyl-phosphonate, Acyl Fluoride, and Aldehyde through the Horner–Wadsworth–Emmons Reaction

Abstract

A novel three-component coupling between trimethylsilylmethylphosphonate, acyl fluoride, and aldehyde has been developed. A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to the acyl fluoride and Horner–Wadsworth–Emmons reaction of an aldehyde with the lithio-<b>β</b>-ketophosphonate generated in situ by desilylation at the α-position of the α-silyl-β-ketophosphonate by fluoride took place cleanly in a one-pot operation. Various <i>E</i>- and <i>Z</i>-enones were obtained in high yields with high stereoselectivities by this one-pot procedure