Chemistry Letters

One-step synthesis of homoterpenoic carboxylic acids from. BETA.-isopropenyl-. BETA.-propiolactone and organocopper reagents.

T Fujisawa, T Sato, M Kawashima, M Nakagawa

Index: Fujisawa, Tamotsu; Sato, Toshio; Kawashima, Masatoshi; Nakagawa, Masakuni Chemistry Letters, 1981 , p. 1307 - 1310

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Citation Number: 11

Abstract

Regioselective reaction of Grignard reagents in the presence of a copper (I) catalyst or of organocuprates with the terminal vinyl carbon of β-isopropenyl-β-propiolactone through the SN 2′ pathway affords 4-methyl-3-alkenoic acids in which the (E)-isomers predominate in good yields. Synthetic utility of this reaction is demonstrated in one-step synthesis of homoterpenoic carboxylic acids.