80959-64-4Relevant articles and documents
Regio- and Stereoselective Ring Opening of ω-Alkenyllactones Using Organocopper Reagents
Kawashima, Masatoshi,Sato, Toshio,Fujisawa, Tamotsu
, p. 3255 - 3264 (2007/10/02)
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 easly obtained in good yields.The ring opening of β-(1-chlorovinyl)-β-propiolactone afforded 4-chloro-3-alkenoic acids which were easly transformed to 4-oxoalkanoic acids and 4-oxo-2-alkenoic acids.
A CONVENIENT METHOD FOR THE SYNTHESIS OF (E)-3-ALKENOIC ACIDS BY A REGIO- AND STEREOSELECTIVE REACTION OF β-VINYL-β-PROPIOLACTONE WITH ORGANOCOPPER REAGENTS
Sato, Toshio,Takeuchi, Masashi,Itoh, Toshiyuki,Kawashima, Masatoshi,Fujisawa, Tamotsu
, p. 1817 - 1820 (2007/10/02)
β-Vinyl-β-propiolactone reacts regio- and stereoselectively with Grignard reagents in the presence of copper(I) catalyst or with diorganocuprates to afford (E)-3-alkenoic acids in high yields.
