JP2001106729A - Optically active polymaleimide derivative, method for producing the same, optical resolution agent consisting of the same and method for resolution of optically active compound using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new optically active polymer useful as an optical resolution agent. SOLUTION: This new polymer, an optically active polymaleimide derivative having an optical rotation of >=190 deg. is obtained by anionic polymerization of the corresponding melamine derivative in the presence of an optically active ligand. The new optically active polymer thus obtained is used as an optical resolution agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an optically active polymaleimide derivative having an optical rotation of 190 ° or more, a method for producing the same, and a separating agent comprising the same. The optically active polymaleimide derivative of the present invention has a high optical rotation and is useful as a separating agent for optically active compounds.

[0002]

2. Description of the Related Art Hitherto, a large number of optically active synthetic polymers used as an optical resolving agent are known, for example, an optically active triphenylmethyl methacrylate polymer (Japanese Patent Application Laid-Open No.
No. 6-106907), an optically active acrylamide polymer (JP-A-56-167708), and a polyacrylamide having an optically active substituent on a side chain chemically bonded to the surface of silica gel (JP-A-63-1446). ) Etc. are known.

[0003]

However, when these optically active polymers are used as a separating agent for optically active compounds, the separation performance of specific compounds is excellent, but the racemic compounds which can be separated are limited. In order to expand the range of application, it is necessary to have a kind of a novel polymer compound having a unique performance.

The present invention has been made to solve the above problems, and an object of the present invention is to provide a novel optically active polymer.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies with the aim of developing a novel optically active polymer, and as a result, have found the optically active polymaleimide derivative of the present invention, which is used as an optical resolving agent. The inventors have found that performance is exhibited, and have completed the present invention.

That is, the present invention provides the following general formula (1)

[0007]

Embedded image

(Wherein R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic group having 6 to 20 carbon atoms) An aromatic hydrocarbon group, a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms 6 to 2 carbon atoms substituted with a substituent selected from the group consisting of
A represents an aromatic hydrocarbon group of 0, A represents a methylene chain having 0 to 5 carbon atoms, n represents a number ranging from 2 to 1000, and * represents an optically active carbon. ), An optically active polymaleimide derivative having an optical rotation of 190 ° or more, a method for producing the same, a separating agent comprising the same, and a method for separating an optically active compound using the same.

The optically active polyimide derivative of the present invention is a compound represented by the above general formula (1).

The method for producing the optically active polyimide derivative is not particularly limited, but for example, the following general formula (2)

[0011]

Embedded image

(Wherein R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic group having 6 to 20 carbon atoms) An aromatic hydrocarbon group, a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms 6 to 2 carbon atoms substituted with a substituent selected from the group consisting of
A represents an aromatic hydrocarbon group of 0, A represents a methylene chain having 0 to 5 carbon atoms, n represents a number ranging from 2 to 1000, and * represents an optically active carbon. Can be prepared by anionic polymerization of the maleimide derivative represented by the formula (1) in the presence of an optically active ligand.

In the present invention, as the maleimide derivative represented by the above general formula (2) as a raw material, specifically, methylmaleimide, ethylmaleimide, n-propylmaleimide, isopropylmaleimide, n-butylmaleimide, n-butylmaleimide Alkylmaleimides such as pentylmaleimide, n-hexylmaleimide, cyclohexylmaleimide, n-heptylmaleimide, n-octylmaleimide, phenylmaleimide, (4-methylphenyl) maleimide, 1-naphthylmaleimide, 2-naphthylmaleimide, 1- Examples include anthrylmaleimide, 2-anthrylmaleimide, 9-anthrylmaleimide, benzylmaleimide, 1-naphthylmethylmaleimide, and 2-naphthylmethylmaleimide.

In the present invention, examples of the anionic polymerization catalyst include alkyl metal catalysts such as n-butyllithium, fluorenyllithium, diethylzinc, and dimethylzinc. The amount used is based on the amount of the starting maleimide derivative used in the reaction. Used in the range of 0.1 to 30 mol%.

In the present invention, the optically active ligand used for anionic polymerization is represented by the following general formula (3):

[0016]

Embedded image

(Wherein R ₂ represents a methyl group, an ethyl group, a straight-chain, branched or cyclic saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic group having 6 to 20 carbon atoms) An aromatic hydrocarbon group, a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms 6 to 2 carbon atoms substituted with a substituent selected from the group consisting of
0 represents an aromatic hydrocarbon group, B represents a methylene chain having 0 to 5 carbon atoms, C represents an alkylidene group or an aromatic group having 1 to 10 carbon atoms, and * represents an optically active carbon. ), The bisoxazoline derivative is added to the anionic polymerization catalyst in an amount of 1 to
Used in the range of 3 mole ratio.

As the bisoxazoline derivative, specifically, (4S) -2,2 '-(1-ethylpropylidene) bis [4- (1-phenylethyl) -4,5-dihydrooxazole], (4S) -2,2 ′-(1-ethylpropylidene) bis [4- (1- (1-naphthyl)
Ethyl) -4,5-dihydrooxazole], (4
S) -2,2 '-(1-Methylethylidene) bis [4-
(1-phenylethyl) -4,5-dihydrooxazole], (4S) -2,2 '-(cyclopropylidene)
Bis [4- (1-phenylethyl) -4,5-dihydrooxazole], (4S) -2,2 '-(1,3-phenyl) bis [4- (1-phenylethyl) -4,5 −
Dihydrooxazole, (4S) -2,2 ′-(2,
6-pyridyl) bis [4- (1-phenylethyl)-
4,5-dihydrooxazole and the like can be mentioned.

As the solvent used for the polymerization in the present invention, any solvent can be used as long as it is inert to the reaction, but usually, the raw materials, catalyst and optically active ligand used in the reaction are sufficiently dissolved. An ether solvent or an aromatic solvent to be used is used. Specifically, ether solvents include diethyl ether, diisopropyl ether, tetrahydrofuran (hereinafter abbreviated as THF) and the like, and aromatic solvents include benzene, toluene, xylene, ethylbenzene and the like. The raw material maleimide derivative used in the reaction is used in an amount of about 1 to 1000 times by weight.

The reaction temperature varies depending on the type of the starting maleimide used in the reaction and the catalyst, and is not particularly limited, but is usually in the range of -78 ° C to 100 ° C.

The reaction time varies depending on the difference between the starting maleimide, the catalyst and the reaction temperature, and is not particularly limited. The reaction is usually completed within a range of 1 hour to 240 hours.

After completion of the reaction, the optically active polymaleimide derivative of the present invention is taken up as a powder by dropping and crystallizing the reaction solution in a solvent having low solubility of products such as hexane, heptane, methanol, ethanol and isopropanol. In order to improve the purity, it may be redissolved in a solvent such as THF or toluene, and then re-dissolved in a solvent such as methanol to perform recrystallization.

The optically active polymaleimide derivative of the present invention can be used as a separating agent for optically active substances.

The method for separating an optically active substance using the optically active polymaleimide derivative of the present invention is not particularly limited. For example, a method in which the optically active polymaleimide derivative of the present invention is supported on a porous carrier. A separating agent is prepared, and the optically active substance can be easily separated by high performance liquid chromatography using a column filled with the separating agent.

The carrier for supporting the optically active polymaleimide derivative of the present invention is not particularly limited, but specifically, silica gel, alumina, cross-linked polystyrene, polysiloxane, and surface-treated with alkylsilane or the like. And the like. The particle size of the carrier is 1 μm to 200 μm, and the average pore size is 10 to 300
0 ° is preferred as a separating agent in high performance liquid chromatography.

The loading method is not particularly limited, but the optically active polymaleimide derivative of the present invention may be brought into contact with a porous carrier to be physically loaded, or the optically active polymaleimide derivative may be produced at the time of production. A functional group may be provided at the terminal of the polymer, and may be chemically bonded to a porous carrier.

The amount of the optically active polymaleimide derivative of the present invention carried on the carrier varies depending on the type and physical properties of the carrier used and is not particularly limited, but is usually 1 to 50% by weight based on the weight of the filler. Can be supported.

The separating agent in which the optically active polymaleimide derivative of the present invention is supported on a porous carrier can be applied to the separation of any optically active compound. For example, when used as a packing material for a column for high performance liquid chromatography, it can be widely applied to any of a normal phase system using hexane-isopropanol as an eluent and a reverse phase system using alcohol-water or the like. In addition, the optically active polymaleimide derivative of the present invention is not limited to use as a packing material for high-performance liquid chromatography, but also has a nuclear magnetic resonance spectrum (NM
It can be used as a shift reagent of R) and also as an optical resolution column support for gas chromatography.

[0029]

According to the present invention, a novel optically active polymer is proposed and can be used as a separating agent for optically active compounds.

[0030]

The present invention will be described in detail with reference to the following examples, but the present invention is not limited to the examples.

The optically active ligand used in the synthesis of the optically active polymaleimide derivative of the present invention: (4S)-
2,2 ′-(1-ethylpropylidene) bis [4- (1
-Phenylethyl) -4,5-dihydrooxazole] (hereinafter abbreviated as (S, S) -Bnbox) is described in S.I.
E. FIG. Denmark, et. al. , J. et al. Org. Ch
em. , 60, 4884 (1995).

The average molecular weight is calculated in terms of polystyrene by gel permeation chromatography (high-speed GPC system manufactured by Tosoh Corporation), and the optical rotation is determined by DIP manufactured by JASCO.
-181.

The separation ability of the prepared optically active polymaleimide derivative was measured by using a multipump CCPM manufactured by Tosoh, an ultraviolet-visible detector UV-8020, and an integrator CHR.
OMATOCORDER21 was used.

Example 1 N-1-naphthylmaleimide (hereinafter abbreviated as 1-NMI) was placed in a 50 ml eggplant-shaped flask containing a magnetic stirrer.
500 mg, diethyl zinc 28 mg, (S, S) -Bn
A box (104 mg) and toluene (15 ml) were charged and reacted at room temperature under stirring for 72 hours.

After completion of the reaction, the reaction solution was poured into 100 ml of methanol, and the precipitate was collected by filtration.
By drying, 0.5 g of the target product, poly (N-1-naphthylmaleimide), was obtained as a slightly yellow powder (yield: 10).
0%).

Optical rotation [α] 435 ²⁵ = + 196.2 °
(C = 1.0 g / dL, THF) Molecular weight Mn = 2100, Mw / Mn = 2.5 Example 2 Using the same apparatus as in Example 1, 1.0 g of 1-NMI, 55 mg of diethyl zinc, (S, S ) -Bnbox 207
mg and 10 ml of tetrahydrofuran, and the mixture was reacted for 96 hours with stirring at room temperature. After the same post-treatment operation as in Example 1, 1.0 g of the target poly (N-1-naphthylmaleimide) was slightly added. Obtained as yellow powder (yield 1
00%).

Optical rotation [α] 435 ²⁵ = + 264.5 °
(C = 1.0 g / dL, THF) Molecular weight Mn = 3100, Mw / Mn = 2.3 Example 3 Using the same apparatus as in Example 1, 1-NMI 500 mg,
Dimethyl zinc 22 mg, (S, S) -Bnbox 10
4 mg and 5 ml of tetrahydrofuran were charged and reacted at room temperature for 72 hours with stirring. After the same post-treatment operation as in Example 1, 0.5 g of the target poly (N-1-naphthylmaleimide) was slightly added. Obtained as yellow powder (yield 1
00%).

Optical rotation [α] 435 ²⁵ = + 246.7 °
(C = 1.0 g / dL, THF) Molecular weight Mn = 5700, Mw / Mn = 3.27 Reference Example 1 Preparation of Silica Gel Treated with Diphenyldichlorosilane Silica gel was put into a 100 ml eggplant-shaped flask equipped with a reflux condenser (Lichrosphere manufactured by Merck).
Si1000, average particle diameter 10 μm, average pore diameter 100
0Å) 5.0 g, diphenyldichlorosilane 4 ml (1
9.3 mmol), 4 ml of triethylamine (28.7).
mmol) and 30 ml of toluene, and reacted under reflux on an oil bath for 24 hours. The reaction product was cooled, poured into 200 ml of methanol, then filtered, washed with methanol, and dried to obtain 6.5 g of silica gel treated with diphenyldichlorosilane.

Example 4 Preparation of silica gel carrying 30% of optically active poly (N-naphthylmaleimide) (rotational angle 195.2 °) and its packed column The optical rotation prepared in Example 1 in a 100 ml eggplant-shaped flask was +195. After 3 g of optically active poly (N-1-naphthylmaleimide) having 2 ° and 50 ml of dichloromethane were charged and dissolved, 7 g of diphenyldichlorosilane-treated silica gel prepared in Reference Example 1 was added, and then dichloromethane was distilled off under reduced pressure using a rotary evaporator. By leaving, 10 g of silica gel carrying 30% of the target substance, optically active poly (N-1-naphthylmaleimide) (195.2 ° optical rotation), was obtained.

The silica gel supporting 30% of the obtained optically active poly (N-1-naphthylmaleimide) (rotational angle: 195.2 °) was dispersed in methanol, and then 2 m stainless steel was used.
A column of mID × 150 mmL was packed using a high-pressure pump at a flow rate of 4.5 ml / min and a maximum pressure of 266 kg / cm ² . The theoretical number of columns of the obtained column was 311.

The number of theoretical plates was measured by using methanol as an eluent and eluting with toluene.
The theoretical plate number was calculated by the following equation.

Theoretical plate number (N) = 5.54 × [Tr / (W1 / 2)] ² Tr = retention time (sec) W1 / 2 = half-width (mm) Example 5 Optically active poly (N-1-) Preparation of silica gel supporting 10% of (naphthylmaleimide) (rotational angle: 246.7 °) and its packed column In the same manner as in Example 4, the optical rotation +
From 1.0 g of optically active poly (N-1-naphthylmaleimide) having 246.7 °, 50 ml of dichloromethane and 9.0 g of the diphenyldichlorosilane-treated silica gel prepared in Reference Example 1, the objective optically active poly (N-1- Naphthylmaleimide) (rotational angle: 246.7 °) 10 g of 10% supported silica gel was obtained.

4.6 mm ID × 250 as in Example 4.
As a result of packing in a stainless steel column of mm and measuring the number of theoretical plates, it was 3103 plates.

Examples 6 to 9 (±) -1,1′-
Separation of binaphthyl-2,2'-diol Using the column prepared in Example 4 or 5, and under the conditions shown in Table 1, (±) -1,1'-binaphthyl-2,
The 2'-diol was separated. The results are shown in Table 1.

[0045]

[Table 1]

Example 10 As in Example 2, 10.0 g of 1-NMI, 550 mg of diethylzinc, 2.0 g of (S, S) -Bnbox and 100 ml of THF were charged into a 500 ml eggplant-shaped flask containing a magnetic stirrer. The reaction was carried out for 96 hours while stirring under room temperature conditions, and after the same post-treatment operation as in Example 1, poly (N-1-naphthylmaleimide) 1
0.0 g was obtained as a slightly yellow powder (yield 100%).

The obtained polymer was further poured into 100 ml of THF / methanol = 3/1 (vol / vol),
After stirring for 1 hour, the insoluble matter was collected by filtration, and the same operation was repeated twice to obtain 3.0 g of purified poly (N-1-naphthylmaleimide) as a slightly yellow powder (yield: 33).
%). The optical rotation of the obtained polymer was [α] 435 ²⁵ = +
718.6 ° (C = 1.0 g / dL, THF).

Example 11 Preparation of silica gel supporting 5% of optically active poly (N-1-naphthylmaleimide) (optical rotation + 718.6 °) and its packed column The optical rotation prepared in Example 10 in a 100 ml eggplant type flask Optically active poly (N-1-) having + 718.6 °
After 0.5 g of naphthylmaleimide) and 50 ml of THF were charged and dissolved, 9.5 g of diphenyldichlorosilane-treated silica gel prepared in the same manner as in Reference Example 1 was added, and then THF was distilled off under reduced pressure using a rotary evaporator. As a result, 10 g of silica gel supporting 5% of optically active poly (N-1-naphthylmaleimide) (rotational angle + 718.6 °) was obtained.

The silica gel supporting 5% of the obtained optically active poly (N-1-naphthylmaleimide) (rotational angle + 718.6 °) was dispersed in methanol, and then 2 m of stainless steel was used.
A column of mID × 150 mmL was packed using a high pressure pump at a flow rate of 2.2 ml / min and a maximum pressure of 170 kg. The number of theoretical plates of the obtained column was 178 as a result of measurement in the same manner as in Example 4.

Examples 12 to 16 Using the column prepared in Example 11, various compounds were separated under the conditions shown in Table 2. The results are shown in Table 2.

[0051]

[Table 2]

Example 17 Using the same reactor as in Example 10, 11.0 g of N-1-anthrylmaleimide, 550 mg of diethylzinc,
2.0 g of (S, S) -Bnbox and THF 100
After the same post-treatment operation as in Example 1, 11.0 g of the target poly (N-1-anthrylmaleimide) was obtained as a slightly yellow powder. (100% yield). The optical rotation of the obtained polymer was [α] 436 ²⁵ = + 210.4 (c = 1.0 g).
/ DL, THF).

Example 18 Preparation of 5% Optically Active Poly (N-1-anthrylmaleimide) (optical rotation + 210.4) -Supported Silica Gel and Its Packed Column The optical rotation prepared in Example 17 in a 100 ml eggplant-shaped flask Optically active poly (N-1-) having + 210.4 °
After charging and dissolving 0.5 g of anthryl maleimide) and 50 ml of THF, diphenyldichlorosilane-treated silica gel (pore diameter 10) prepared by the same operation as in Reference Example 1 was used.
0 °) 9.5 g, and then THF was distilled off under reduced pressure using a rotary evaporator to obtain the desired optically active poly (N-1-anthrylmaleimide) (rotational power +21).
0.4 °) 10 g of 5% supported silica gel were obtained.

The silica gel supporting 5% of the obtained optically active poly (N-1-anthrylmaleimide) (rotational angle + 210.4 °) was dispersed in methanol, and then the dispersion was made of stainless steel.
Using a high pressure pump for the column of mmID x 150mmL,
The filling was performed at a flow rate of 3.35 ml / min and a maximum pressure of 400 kg. The number of theoretical plates of the obtained column was 200 as a result of measurement in the same manner as in Example 4.

Example 19 Separation of racemic epoxy chalcone was examined using the column prepared in Example 18 at a mobile phase of [hexane / isopropanol = 8/2 (vol / vol)] at a flow rate of 0.1 ml / min. However, the separation coefficient α was 1.25.

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[Procedure amendment]

[Submission Date] August 7, 2000 (2000.8.7)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Claims

[Correction method] Change

[Correction contents]

[Claims]

Embedded image (Wherein, R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms,
A linear, branched or cyclic unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms,
Or a methyl group, an ethyl group, a straight-chain, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, 3 to 8 carbon atoms
Linear, branched or cyclic unsaturated aliphatic hydrocarbon groups, and C6-C20 aromatics substituted with a substituent selected from the group consisting of C6-C20 aromatic hydrocarbon groups. A represents a methylene chain having 0 to 5 carbon atoms;
n is a number in the range of 2 to 1000, and * represents optically active carbon. ), Having an optical rotation of 190 ° or more.

Embedded image (Wherein, R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms,
A linear, branched or cyclic unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms,
Or a methyl group, an ethyl group, a straight-chain, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, 3 to 8 carbon atoms
Linear, branched or cyclic unsaturated aliphatic hydrocarbon groups, and C6-C20 aromatics substituted with a substituent selected from the group consisting of C6-C20 aromatic hydrocarbon groups. And A represents a methylene chain having 0 to 5 carbon atoms. The maleimide derivative represented by the following general formula (3)

Embedded image (Wherein, R ₂ is a methyl group, an ethyl group, a linear, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms,
A linear, branched or cyclic unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms,
Or a methyl group, an ethyl group, a straight-chain, branched or cyclic saturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, 3 to 8 carbon atoms
Linear, branched or cyclic unsaturated aliphatic hydrocarbon groups, and C6-C20 aromatics substituted with a substituent selected from the group consisting of C6-C20 aromatic hydrocarbon groups. B represents a methylene chain having 0 to 5 carbon atoms;
C is an alkylidene group or an aromatic group having 1 to 10 carbon atoms, *
The mark represents optically active carbon. 2. The method for producing an optically active polymaleimide derivative according to claim 1, wherein anion polymerization is carried out in the presence of the bisoxazoline derivative represented by the formula (1).

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0007

[Correction method] Change

[Correction contents]

[0007]

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[Procedure amendment 3]

[Document name to be amended] Statement

[Correction target item name] 0011

[Correction method] Change

[Correction contents]

[0011]

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Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) C08L 35/00 C08L 35/00 G01N 30/48 G01N 30/48 W // C07D 207/404 C07D 207/404 317/18 317/18

Claims (6)

[Claims] [Claim 1] The following general formula (1) (Wherein R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms) Hydrogen group,
Or a group consisting of a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms. Represents an aromatic hydrocarbon group having 6 to 20 carbon atoms substituted by a substituent represented by the following formula: A is a methylene chain having 0 to 5 carbon atoms, n
Represents a number in the range of 2 to 1,000, and * represents optically active carbon. ), Having an optical rotation of 190 ° or more. 2. The following general formula (2): (Wherein R ₁ is a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms) Hydrogen group,
Or a group consisting of a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms. A represents an aromatic hydrocarbon group having 6 to 20 carbon atoms, and A represents a methylene chain having 0 to 5 carbon atoms. )
A maleimide derivative represented by the following general formula (3): (Wherein R ₂ represents a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms) Hydrogen group,
Or a group consisting of a methyl group, an ethyl group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having 3 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms. Represents an aromatic hydrocarbon group having 6 to 20 carbon atoms and substituted with a substituent, wherein B is a methylene chain having 0 to 5 carbon atoms,
Represents an alkylidene group or an aromatic group having 1 to 10 carbon atoms, and * represents an optically active carbon. 2. The method for producing an optically active polymaleimide derivative according to claim 1, wherein anion polymerization is carried out in the presence of the bisoxazoline derivative represented by the formula (1). 3. A separating agent comprising the optically active polymaleimide according to claim 1. 4. A separating agent comprising the optically active polymaleimide according to claim 1 supported on a carrier. 5. An optically active compound comprising a separating agent comprising the optically active polymaleimide according to claim 1 or a separating agent comprising the optically active polymaleimide according to claim 1 supported on a carrier. Separation method. 6. An optically active compound, wherein the optically active compound is separated by high performance liquid chromatography using a column filled with a separating agent comprising the optically active polymaleimide according to claim 1 supported on a carrier. Separation method.