Journal of Organic Chemistry p. 2798 - 2802 (1989)
Update date:2022-08-03
Topics:
Nowick, James S.
Danheiser, Rick L.
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.
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