Method of producing optically active compound

An optically active compound production method using a column reactor prepared by charging a column for the column reactor with asymmetric catalyst particles, wherein

• the asymmetric catalyst particles have an average particle diameter of 1 to 10 μm as measured by a flow type particle image analysis method and are resin particles prepared from a monomer composition containing, as a monomer having a chiral source, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-trans-4-hydroxy-L-proline, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-cis-4-hydroxy-D-proline, or N-tert-butyloxycarbonyl-O-(4-vinylbenzyl)-trans-4-hydroxy-L-proline, divinylbenzene as a polyunsaturated compound monomer, and further containing a radical polymerization initiator, the resin particles being capable of serving as a catalyst for an aldol reaction, and
• reaction compounds comprising cyclohexanone as a carbonyl compound having an α hydrogen and one of 4-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 4-trifluoromethylbenzaldehyde are introduced into the column reactor to bring the reaction compounds into contact with the asymmetric catalyst particles, whereby the reaction compounds are converted to an optically active compound, the optically active compound being 2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one, 2-(hydroxy(3-nitrophenyl)methyl)cyclohexan-1-one, or 2-(hydroxy(4-trifluoromethylphenyl)methyl)cyclohexan-1-one.

An optically active compound production method using a column reactor prepared by charging a column for the column reactor with asymmetric catalyst particles, wherein:

• the asymmetric catalyst particles have an average particle diameter of 1 to 10μm as measured by a flow type particle image analysis method and are resin particles prepared from a monomer composition containing, as a monomer having a chiral source, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-trans-4-hydroxy-L-proline, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-cis-4-hydroxy-D-proline, or N-tert-butyloxycarbonyl-O-(4-vinylbenzyl)-trans-4-hydroxy-L-proline, divinylbenzene as a polyunsaturated compound monomer, and further containing a radical polymerization initiator, the resin particles being capable of serving as a catalyst for an aldol reaction;
• and
• reaction compounds comprising cyclohexanone as a carbonyl compound having an α hydrogen and one of 4-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 4-trifluoromethylbenzaldehyde are introduced into the column reactor to bring the reaction compounds into contact with the asymmetric catalyst particles, whereby the reaction compounds are converted to an optically active compound, the optically active compound being 2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one, 2-(hydroxy(3-nitrophenyl)methyl)cyclohexan-1-one, or 2-(hydroxy(4-trifluoromethylphenyl)methyl)cyclohexan-1-one;
• and
• the optically active compound is further subjected to optical resolution in the column reactor.

An optically active compound production method using a column reactor prepared by charging a column for the column reactor with asymmetric catalyst particles, wherein:

• the asymmetric catalyst particles have an average particle diameter of 1 to 10μm as measured by a flow type particle image analysis method and are resin particles prepared by a micro-channel method including:
• injecting a monomer composition into a continuous phase to thereby form droplets of the monomer composition in the continuous phase, the monomer composition containing, as a monomer having a chiral source, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-trans-4-hydroxy-L-proline, N-tert-butyloxycarbonyl-O-(2-methacryloyloxyethylsuccinoyl)-cis-4-hydroxy-D-proline, or N-tert-butyloxycarbonyl-O-(4-vinylbenzyl)-trans-4-hydroxy-L-proline divinylbenzene as a polyunsaturated compound monomer, and further containing a radical polymerization initiator;
• and then heating the droplets to cause such a proline derivative monomer having an unsaturated bond to undergo radical polymerization, the resin particles being capable of serving as a catalyst for an aldol reaction;
• reaction compounds comprising cyclohexanone as a carbonyl compound having an α hydrogen and one of 4-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 4-trifluoromethylbenzaldehyde are introduced into the column reactor to bring the reaction compounds into contact with the asymmetric catalyst particles, whereby the reaction compounds are converted to an optically active compound, the optically active compound being 2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one, 2-(hydroxy(3-nitrophenyl)methyl)cyclohexan-1-one, or 2-(hydroxy(4-trifluoromethylphenyl)methyl)cyclohexan-1-one;
• and
• the optically active compound is further subjected to optical resolution in the column reactor.