SIMPLE METHODS FOR, THE SYNTHESIS OF (E)-4- AND (E)-5-ALKENOIC ACIDS BY THE SN2' TYPE REACTIONS OF γ-VINYL-γ-BUTYROLACTONE AND δ-VINYL-δ-VALEROLACTONE WITH ORGANOCOPPER REAGENTS

Article abstract of DOI:10.1016/S0040-4039(00)87676-5

γ-Vinyl-γ-butyrolactone and δ-vinyl-δ-valerolactone react regio- and stereoselectively with Grignard reagents in the presence of a copper(I) catalyst or with diorganocuprates to afford (E)-4- and (E)-5-alkenoic acids, respectively, in high yields.Synthetic utility of the former reaction is demonstrated in the simple synthesis of (4E,7Z)-4,7-tridecadienyl acetate.