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 |
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Authors: | Tamotsu Fujisawa Toshio Sato Masatoshi Kawashima Kouichi Naruse Kouichi Tamai |
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Affiliation: | Chemistry Department of Resources, Mie University, Tsu, Mie 514, Japan |
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Abstract: | γ-Vinyl-γ-butyrolactone and δ-vinylδ-valerolactone react regio- and stereoselectivity 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. |
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