Regio- and stereoselective ring opening of .OMEGA.-alkenyllactones using organocopper reagents.

概要

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New synthetic methods are described for the preparation of (E)-3-, (E)-4-, and (E)-5-alkenoic acids by the regio- and stereoselective ring opening of β, γ, and δ-lactones with unsaturated substituents at the ω-position using organocopper reagents such as halomagnesium diorganocuprates or Grignard reagents in the presence of copper(I) iodide. Both the organocopper reagents with primary, secondary, tertiary alkyl, and phenyl groups gave the corresponding carbon homologated alkenoic acids in good yields. Alkadienoic acids were also obtained in good yields by the reactions of ω-alkenyllactones with divinyl- and diallylcuprates. Utilizing the ring opening of β-isopropenyl-β-propiolactone, homoterpenoid carboxylic acids were easily obtained in good yields. The ring opening of β-(1-chlorovinyl)-β-propiolactone afforded 4-chloro-3-alkenoic acids which were easily transformed to 4-oxoalkanoic acids and 4-oxo-2-alkenoic acids.
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