JP2009215222A5 - - Google Patents

Description

（Ｒ^１は置換基を有していても良い脂肪族基、又は置換基を有していても良い芳香族基を示し、Ｒ^１同士は結合して環を形成していてもよく；Ｒ^２は置換基を有していてもよい芳香族基、又は置換基を有していても良い脂肪族基を示す）で表されるアジリジン化合物と、式II

（Ｒ^３は置換基を有していても良い脂肪族基、置換基を有していても良い芳香族基、ハロゲン、アルキルオキシ、アリールオキシ、又はニトロ基）で表されるアニリン誘導体とを反応させることを特徴とする。 As a result of examining various asymmetric ligands, the present inventors have found that a tridentate binaphthol derivative is effective. In addition, as a result of investigations using various metals, it was found that early transition metals, particularly titanium, zirconium and hafnium belonging to Group 4, are more effective catalysts.
The method for producing an optically active 1,2-diamine compound of the present invention comprises a triol comprising a titanium, zirconium, or hafnium compound and an optically active binaphthol derivative consisting of an (R) -form or (S) -form or an enantiomer thereof. In a reaction system obtained by mixing the body with an organic solvent.

(R ¹ represents an aliphatic group which may have a substituent, or an aromatic group which may have a substituent, and R ¹ may be bonded to each other to form a ring; R ² represents an aromatic group which may have a substituent, or an aliphatic group which may have a substituent, and a formula II

An aniline derivative represented by (R ³ is an aliphatic group which may have a substituent, an aromatic group which may have a substituent, a halogen, an alkyloxy, an aryloxy, or a nitro group). It is made to react.

で表され（式中、Ｙは２価の炭化水素基を表し；R⁴, R⁵は同じでも異なっていてもよい、水素原子、炭素数１〜６の炭化水素基、ハロゲン基、又は炭素数１〜６のパーフルオロアルキル基を表す）、（Ｒ）−体又は（Ｓ）−体からなり光学活性なビナフトール誘導体を含むトリオール又はその対掌体とを混合してなることを特徴とする光学活性触媒。 The optically active catalyst of the present invention comprises a titanium, zirconium, or hafnium compound, and a compound of formula III

(Wherein Y represents a divalent hydrocarbon group; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or carbon; A triol containing an optically active binaphthol derivative or an enantiomer thereof, which is composed of (R) -form or (S) -form Optically active catalyst.

（式中、nは０-２の整数を表し；R⁴, R⁵は同じでも異なっていてもよい、水素原子、炭素数１〜６の炭化水素基、ハロゲン基、又は炭素数１〜６のパーフルオロアルキル基を表し；R⁶は水素原子、炭素数１〜６の炭化水素基、ハロゲン基、又は炭素数１〜６のパーフルオロアルキル基を表し；R⁷は水素原子または炭素数１〜６の炭化水素基を表す）で表され、（Ｒ）−体又は（Ｓ）−体からなり光学活性なビナフトール誘導体を含むトリオール又はその対掌体とを混合してなることを特徴とする。


The optically active catalyst of the present invention comprises a titanium, zirconium, or hafnium compound, and a compound of formula IV

(In the formula, n represents an integer of 0-2; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or 1 to 6 carbon atoms. R ⁶ represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or a perfluoroalkyl group having 1 to 6 carbon atoms; R ⁷ represents a hydrogen atom or 1 carbon atom. And a triol containing an optically active binaphthol derivative or an enantiomer thereof, which is composed of (R) -isomer or (S) -isomer, .

Claims (6)

In a reaction system obtained by mixing a titanium, zirconium, or hafnium compound with a triol comprising an (R) -isomer or (S) -isomer and containing an optically active binaphthol derivative or an enantiomer thereof in an organic solvent. , Formula I

(R ¹ represents an aliphatic group which may have a substituent, or an aromatic group which may have a substituent, and R ¹ may be bonded to each other to form a ring; R ² represents an aromatic group which may have a substituent, or an aliphatic group which may have a substituent, and a formula II

An aniline derivative represented by (R ³ is an aliphatic group which may have a substituent, an aromatic group which may have a substituent, a halogen, an alkyloxy, an aryloxy, or a nitro group). A method for producing an optically active 1,2-diamine compound, characterized by reacting. The method for producing an optically active 1,2-diamine compound according to claim 1, wherein the titanium, zirconium, or hafnium compound is an alkoxide or a halogen compound. The triol is of formula III

(Wherein Y represents a divalent hydrocarbon group; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or The method for producing an optically active 1,2-diamine compound according to claim 1 or 2, which represents a C 1-6 perfluoroalkyl group. The triol is of formula IV

(In the formula, n represents an integer of 0-2; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or 1 to 6 carbon atoms. R ⁶ represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or a perfluoroalkyl group having 1 to 6 carbon atoms; R ⁷ represents a hydrogen atom or 1 carbon atom. The method for producing an optically active 1,2-diamine compound according to claim 1 or 2, which represents a hydrocarbon group of -6. A titanium, zirconium, or hafnium compound and the formula III

(Wherein Y represents a divalent hydrocarbon group; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or carbon; A triol containing an optically active binaphthol derivative or an enantiomer thereof, which is composed of (R) -form or (S) -form Optically active catalyst. Titanium, zirconium, or hafnium compound and formula IV

(In the formula, n represents an integer of 0-2; R ⁴ and R ⁵ may be the same or different, a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or 1 to 6 carbon atoms. R ⁶ represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogen group, or a perfluoroalkyl group having 1 to 6 carbon atoms; R ⁷ represents a hydrogen atom or 1 carbon atom. And a triol containing an optically active binaphthol derivative or an enantiomer thereof, which is composed of (R) -isomer or (S) -isomer, Optically active catalyst.