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AssigneeSumitomo Chemical Company, Limited
InventorsKanji Nishizawa, Satoshi Mitsuda, Ryohei Komaki, Masako Sugimoto, Chiaki Sugiki, Yasutaka Ogami, Kazumi Sonoda, Fumitaka Kishimoto
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The present relates to a process for preparing optically active cyclopropane carboxylic acid derivatives of salts thereof represented by the formula (III) ##STR1## wherein X is chlorine atom, bromine atom, methyl group or trifluoromethyl group and R' is hydrogen atom or metal ion, by asymmetrically hydrolyzing cyclopropane carboxylic acid esters having the formula (II) ##STR2## wherein X is as defined above and R is C.sub.1-4 alkyl group or halogen-substituted C.sub.1-4 alkyl group with specific strains of microorganisms or esterase derived therefrom.
A process for producing an optically active (+)-cis-cyclopropane carboxylic acid or derivatives thereof, which comprises allowing a (.+-.)-cis-cyclopropane carboxylic acid ester represented by formula (IV), ##STR14## wherein X is selected from the group consisting of a chlorine atom, a bromine atom, a methyl group, and a trifluoromethyl group, and R is selected from the group consisting of a C.sub.1 -C.sub.4 alkyl group and a C.sub.1 -C.sub.4 alkyl group substituted with a halogen atom, to react with a microorganism selected from the group consisting of
A process for producing a (+)-cis-cyclopropane carboxylic acid or derivatives thereof represented by formula (V), ##STR16## wherein R' is selected from the group consisting of a hydrogen atom and a metal ion, which comprises allowing a (.+-.)-cis-cyclopropane carboxylic acid ester of formula (VI), ##STR17## wherein R is selected from the group consisting of a C.sub.1 -C.sub.4 alkyl group and a C.sub.1 -C.sub.4 alkyl group substituted by a halogen atom, to react with Arthrobacter globiformis IFO-12958 or an esterase produced thereby which can perform this hydrolysis, and then recovering said (+)-cis-cyclopropane carboxylic acid or derivatives thereof represented by formula (V).
A process for producing a (+)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid or salts thereof, which comprises allowing a (.+-.)-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid ester represented by formula (VIII), ##STR18## wherein R is selected from the group consisting of a C.sub.1 -C.sub.4 alkyl group and a C.sub.1 -C.sub.4 alkyl group substituted with a halogen atom, to react with Arthrobacter globiformis IFO-12958 or an esterase produced thereby which can perform this hydrolysis, to asymmetrically hydrolyze said ester thereby forming said (+)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid salts thereof and the ester of its diastereomer, and then recovering said (+)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid or salts thereof.
Dependencies are inferred from the claim text.