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 …
T Fujisawa, T Sato, M Kawashima, K Naruse…
Index: Fujisawa, Tamotsu; Sato, Toshio; Kawashima, Masatoshi; Naruse, Kouichi; Tamai, Kouichi Tetrahedron Letters, 1982 , vol. 23, # 35 p. 3583 - 3586
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Citation Number: 25
Abstract
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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