Ruthenium-diamine complexes and method for producing optically active compounds

A ruthenium complex represented by the following formula (2):

• wherein symbol * represents an asymmetric carbon atom;
• R1 represents an alkyl group having 1 to 10 carbon atoms;
• a halogenated alkyl group having 1 to 10 carbon atoms;
• 10-camphoryl group;
• an amino group which may be substituted with one or two alkyl group having 1 to 10 carbon atoms;
• an aryl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a halogen atom, a cyano group (—CN), an amino group, an alkylated amino group (—NR20R21), a five or six membered cyclic amino group, an acylated amino group (—NH—CO—R20), a hydroxyl group, an alkoxy group (—OR20), an acyl group (—CO—R20), a carboxyl group, an alkoxycarbonyl group (—COOR20), a phenoxy carbonyl group, a mercapto group, an alkylthio group (—SR20), a silyl group (—SiR20R21R22), or a nitro group (—NO2);
• R20, R21 and R22 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
• Y represents a hydrogen atom;
• R2 and R3 each independently represent a hydrogen atom;
• an alkyl group having 1 to 10 carbon atoms;
• a phenyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom;
• or a cycloalkyl group having 3 to 8 carbon atoms, or R2 and R3 may be joined together to form a ring;
• R11, R12, R13, R14 and R15 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms;
• R16, R17, R18 and R19 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or R16 and R17 with the carbon atom which is substituted with R16 and R17, and/or R18 and R19 with the carbon atom which is substituted with R18 and R19 may form a carbonyl group(s);
• Z represents an oxygen atom or a sulfur atom;
• Q− represents a counter anion;
• and
• n1 represents 1 or 2, and n2 represents an integer from 1 to 3.

A ruthenium complex represented by the following formula (3):

• wherein symbol * represents an asymmetric carbon atom;
• R1 represents an alkyl group having 1 to 10 carbon atoms;
• a halogenated alkyl group having 1 to 10 carbon atoms;
• 10-camphoryl group;
• an amino group which may be substituted with one or two alkyl group having 1 to 10 carbon atoms;
• an aryl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a halogen atom, a cyano group (—CN), an amino group, an alkylated amino group (—NR20R21), a five or six membered cyclic amino group, an acylated amino group (—NH—CO—R20), a hydroxyl group, an alkoxy group (—OR20), an acyl group (—CO—R20), a carboxyl group, an alkoxycarbonyl group (—COOR20), a phenoxy carbonyl group, a mercapto group, an alkylthio group (—SR20), a silyl group (—SiR20R21R22), or a nitro group (—NO2);
• R20, R21 and R22 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
• Y represents a hydrogen atom;
• R2 and R3 each independently represent a hydrogen atom;
• an alkyl group having 1 to 10 carbon atoms;
• a phenyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom;
• or a cycloalkyl group having 3 to 8 carbon atoms, or R2 and R3 may be joined together to form a ring;
• R11, R12, R13, R14 and R15 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms;
• R16, R17, R18 and R19 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or R16 and R17 with the carbon atom which is substituted with R16 and R17, and/or R18 and R19 with the carbon atom which is substituted with R18 and R19 may form a carbonyl group(s);
• Z represents an oxygen atom or a sulfur atom;
• V represents a halogen atom;
• and
• n1 represents 1 or 2, and n2 represents an integer from 1 to 3.