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US 8,013,171 B2Granted
Axially asymmetric ester compound and production method thereof
AssigneesNational University Corporation Tokyo University of Agriculture and Technology, Takasago International Corporation
InventorKen Tanaka
Life of this patent
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Abstract
To provide an axially asymmetric optically active biaryl ester compound that can easily produced without the step of optical resolution which was almost indispensable in conventional methods. There is provided a method for producing an axially asymmetric ester compound, comprising a cycloaddition of a compound having a triple bond with the use of a catalyst containing rhodium metal and an optically active bisphosphine.
Claims2
An optically active compound represented by the following general formula (4′):
- wherein, R1 and R2 may be the same or different and are hydrogen atom, an alkali metal, or an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms;
- R11 is hydrogen atom, an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, a cycloalkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, or an aryl group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms;
- R12′ is an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, a cycloalkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, or an aryl group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms;
- Z1 is an oxygen, a sulfur atom, a methylene chain, NRN (wherein RN is alkyl, aryl, alkanesulfonyl, arylsulfonyl, or acyl group) or Si(RSi)2 (wherein RSi is an alkyl or aryl group or may form a ring as Si(RSi)2;
- two R12′ may form a ring optionally having a substituent selected from the group consisting alkyl groups, alkoxy groups and halogen atoms, or a methylene chain optionally having a substituent selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkoxycarbonyl groups having an alkoxy group having 1 to 4 carbon atoms and halogen atoms and optionally having oxygen atom or sulfur atom in the chain, in combination with each other;
- and * is axial asymmetry.
3 more elements
An optically active compound represented by the following general formula (8′):
- wherein, R1 is hydrogen atom, alkali metal, or an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms;
- RM is hydrogen atom or a protecting group of hydroxyl group;
- R7, R8 and R9 are independently hydrogen atom, an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, a cycloalkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, an aryl group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms, an alkoxy group optionally having a substituent selected from the group consisting of halogen atoms and aryl groups, or an aryloxy group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms;
- R11 is a hydrogen atom, an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, a cycloalkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, or an aryl group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms;
- R10′ and R12′ are independently an alkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, a cycloalkyl group optionally having a substituent selected from the group consisting of alkoxy groups and halogen atoms, or an aryl group optionally having a substituent selected from the group consisting of linear or branched alkyl groups having 1 to 6 carbon atoms, linear or branched alkoxy groups having 1 to 6 carbon atoms and halogen atoms;
- any two adjacent groups among R7, R8 and R9 may form an aromatic ring optionally having a substituent selected from the group consisting of alkyl groups, alkoxy groups and halogen atoms, a methylene chain optionally having a substituent selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkoxycarbonyl groups having an alkoxy group having 1 to 4 carbon atoms and halogen atoms, or a (poly)methylenedioxy group optionally having a substituent selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkoxycarbonyl groups having an alkoxy group having 1 to 4 carbon atoms and halogen atoms;
- Z1 is an oxygen, a sulfur atom, a methylene chain, NRN (wherein RN is alkyl, aryl, alkanesulfonyl, arylsulfonyl, or acyl group) or Si(RSi)2 (wherein RSi is an alkyl or aryl group or may form a ring as Si(RSi)2;
- and * is axial asymmetry.
5 more elements
Dependencies are inferred from the claim text.