- Stereoselective synthesis of cis -2-fluorocyclopropanecarboxylic acid
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A rhodium-catalyzed cyclopropanation of 1-fluoro-1-(phenylsulfonyl)ethylene and diazo esters is described as an effective method for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid. This process provides an example of the cyclopro
- Shibue, Taku,Fukuda, Yasumichi
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p. 7226 - 7231
(2014/08/18)
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- PROCESS FOR PRODUCING 1,2-CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ESTER COMPOUND
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Provided is an industrially applicable process for producing 1,2-cis-2-fluorocyclopropane-1-carboxylic ester. A process for producing a compound represented by formula (3): [wherein R 1 represents, for example, a C1-C8 alkyl group], which process includes reacting a compound represented by formula (1) : [wherein X 1 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 1 and X 2 are not simultaneously hydrogen atoms; and R 1 has the same meaning as defined in formula (3)] with a reducing agent represented by formula (2): €?€?€?€?€?€?€?€?M 1 BH m R 2 n (2-1) or M 2 (BH m R 2 n ) 2 €?€?€?€?€?(2-2) [wherein M 1 represents an alkali metal atom; M 2 represents an alkaline earth metal atom or a zinc atom; R 2 represents, for example, a hydrogen atom; m represents an integer from 1 to 4; n represents an integer from 0 to 3; and the sum of m and n is 4] in the presence of an aprotic polar solvent, and a Lewis acid such as a halide of an atom selected from among, for example, boron, magnesium, and aluminum.
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Page/Page column 12-13
(2008/06/13)
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- PROCESS FOR REDUCTIVE DEHALOGENATION
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A method ofproducing2-fluorocyclopropane-1-carboxylic acid ester, which comprise by allowing a compound represented by the following formula (1): wherein X represents a chlorine atom, a bromine atom or an iodine atom; and R1 represents an alkyl
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Page/Page column 4-5
(2008/06/13)
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- A novel stereoselective synthesis of cis-2-fluoro-cyclopropane-1-carboxylic acid
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A novel method consisting four-step from tert-butyl acrylate (4) and chloromethyl phenyl sulfoxide (5) for preparing cis-2-fluorocyclopropane-1-carboxylic acid (cis-3) was elaborated. The method involves initial formation of the cis-2-phenylsulfinylcyclopropanecarboxylate (cis-6), fluorination by molecular fluorine to trans-7, reductive desulfonylation to the ester (cis-9) and acid-catalyzed hydrolysis to the final product (cis-3).
- Toyota, Akemi,Ono, Yoshinori,Kaneko, Chikara,Hayakawa, Isao
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p. 8507 - 8510
(2007/10/03)
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