Method for producing axial asymmetric compounds, and intermediates for producing the same

A method for producing a 2-amino-2′-diarylphosphinyl-1,l′-binaphthyl represented following formula (1)

• wherein each Ar represents an aryl group which may be substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy group, with both Ar's being the same or different from each other;
• n represents 1;
• R1 and l2 represent hydrogen atoms by effecting a strong alkaline reagent on an aminophosphine oxide represented by the following formula (1)
• wherein Ar is the same as above;
• n represents 1;
• and
• one of R1 and R2 represents a hydrogen atom and the other represents —COR3 wherein R3 represents a lower alkoxy group having 1 to 4 carbon atoms in an alcohol.

A method for producing an aminophosphine compound or an aminophosphine oxide compound represented by the following formula (1)

• wherein each Ar represents an aryl group which may be substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy group, with both Ar's being the same or different from each other;
• R1 and R2 represent hydrogen atoms;
• and
• n represents 0 or 1 with a halide represented by the following formula (6)
• RX (6)
• wherein X represents Cl or Br;
• and
• R represents —COR3 wherein R3 represents a cycloalkyl group having 5 to 7 carbon atoms, a lower alkyl group having 1 to 6 carbon atoms which may be substituted with a halogen atom, a lower alkoxy group or a phenyl group, a substituted or unsubstituted phenyl group, or a lower alkoxy group having 1 to 6 carbon atoms which may be substituted with a cycloalkyl group having 5 to 7 carbon atoms, a halogen atom, a lower alkoxy group or phenyl group or —SO2R4 wherein R4 represents a cycloalkyl group having 5 to 7 carbon atoms, an alkyl group having 1 to 6 carbon atoms which may be substituted with a halogen atom, a lower alkoxy group or phenyl group, or substituted or unsubstituted phenyl group in the presence of a base in an organic solvent.

A method for producing an aminophosphine compound represented by the following formula (1-0):

• wherein each Ar represents an aryl group which may be substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy group with both Ar's being the same or different from each other;
• n represents 0;
• R3 represents a cycloalkyl group having 5 to 7 carbon atoms, a lower alkyl group having 1 to 6 carbon atom which may be substituted with a halogen atom, a lower alkoxy group or phenyl group, or substituted or unsubstituted phenyl group;
• the method comprising the steps of:
• dissolving an aminophosphine compound or an aminophosphine oxide compound represented by the following formula (1)
• wherein each Ar represents an aryl group which may be substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy group with both Ar's being the same or different from each other;
• n represents 0 or 1;
• and
• one of R1 and R2 represents a hydrogen atom and the other represents —COR3 wherein R3 represents a cycloalkyl group having 5 to 7 carbon atoms, a lower alkyl group having 1 to 6 carbon atoms which may be substituted with a halogen atom, a lower alkoxy group or phenyl group, or a substituted or unsubstituted phenyl group into an organic solvent to obtain a solution;
• adding a borane-dimethyl sulfide complex to said solution to react them with each other to obtain a reaction solution;
• subjecting said reaction mixture to evaporation to obtain residue;
• adding a tertially amine to said residue to react them with each other;
• and
• evaporating said tertially amine.

A method for producing an aminophosphine compound represented by the following formula (1)

• wherein each Ar represents an aryl group which may be substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy group with both Ar's being the same or different from each other;
• n represents 0;
• and
• one of R1 and R2 represents a hydrogen atom and the other represents a methyl group;
• the method comprising the steps of:
• dissolving an aminophosphine compound or an aminophosphine oxide compound represented by the following formula (1)
• wherein each Ar is the same as above;
• n represents 0 or 1;
• and
• one of R1 and R2 represents a hydrogen atom and the other represents —COR3 wherein R3 represents a lower alkoxy group into an organic solvent to obtain a solution;
• adding a borane-simethylsulfide complex to said solution to react them with each other to obtain reaction solution;
• subjecting said reaction solution to evaporation to provide residue;
• adding a tertially amine to said residue to react them with each other;
• and
• evaporating said tertially amine.