Application of (α-Phosphonoacyl)silane Reagents to the Synthesis of α,β-Unsaturated Acylsilanes

Article abstract of DOI:10.1021/jo00273a007

An efficient and convergent synthetic route to α,β-unsaturated acylsilanes has been developed based on the Horner-Wadsworth-Emmons reaction of (α-phosphonoacyl)silanes.The Arbuzov reaction of the (α-iodoacyl)silane 1c with trimethyl phosphite provides access to the phosphonate 2, which can be alkylated by treatment with potassium tert-butoxide and methyl iodide to afford 3.These (α-phosphonoacyl)silane reagents combine smoothly with a variety of aldehydes to furnish α,β-unsaturated acylsilanes 5-13 in good to excellent yield.