Preparation of optically active cyclopentenolone

Abstract

Abstract PURPOSE: To obtain the titled optically active compound useful as an intermediate for an insecticide, by hydrolyzing a diastereomer salt obtained by the reaction of an acid phthalic acid ester of the titled optically inactive compound with a specific optically active compound, under specific conditions. CONSTITUTION: A compound containing a racemate or partly an optically active substance of formula I, is reacted with an optically active α-phenyl-β-p-tolylethylamine, to form a diastereomer salt, from which the optically active compound of formula I is separated with their solubility difference. The resulting compound is hydrolyzed in water or a solvent containing water, in the presence (absence) of a base in a small excess or less of theoretical amount, to prepare an optically active 4- hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenolone of formula II. The compound may be converted to a compound of formula III etc., useful as an insecticide, especially the (+)- optically active substance with a powerful insecticidal activity. COPYRIGHT: (C)1981,JPO&Japio

Inventors

• 👤 Takashi Matsuo
• 👤 Kazuhiro Tsushima

Bibliographic Details