Simple methods for the syntheses 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

✍ Scribed by Tamotsu Fujisawa; Toshio Sato; Masatoshi Kawashima; Kouichi Naruse; Kouichi Tamai

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 249 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87676-5

✦ Synopsis

y-Vinyl-y-butyrolactone a& &vinyl-A-valeroZactone react regio-and stereosetectively with Grignard reagents in the presence of a copper(I) catalyst or with cliorganocuprates to afford IE)-4-and (El-S-alkenoic acids, respectively, in high yields. Synthetic utility

of the former reaction is demonstrated in the simple synthesis of (4E,72)-4,7-tridecadienyl acetate.