A NOVEL FIVE-CARBON HOMOLOGATION LEADING TO 3,4-ALKADIENOIC ACIDS BY SN2' REACTION OF β-ETHYNYL-β-PROPIOLACTONE WITH GRIGNARD REAGENTS IN THE PRESENCE OF COPPER(I) CATALYST

Article abstract of DOI:10.1016/S0040-4039(01)82911-7

β-Ethynyl-β-propiolactone reacts regioselectively with Grignard reagents in the presence of copper(I) catalyst to afford 3,4-alkadienoic acids in high yields.Synthetic utility of this reaction is demonstrated in the simple synthesis of pellitorine.