Chiral iridium aqua complex and method for producing optically active hydroxy compound by using the same

A method of producing a chiral iridium aqua complex represented by the formula (5):

• wherein
• R7 is an aryl group substituted by haloalkyl group(s) having 1 to 6 carbon atoms,
• R8 and R9 are the same or different and each is an aralkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group, or an alkyl group or a hydrogen atom,
• X is a monovalent or divalent anion, and
• n is 2 when X is a monovalent anion, or n is 1 when X is a divalent anion,
• which comprises reacting an iridium complex represented by the formula (10):
• wherein X and n are as defined above,
• with a chiral diamine represented by the formula (11):
• wherein R7, R8 and R9 are as defined above.

A method of producing an optically active hydroxy compound represented by the formula (7):

• wherein
• R5 is an aryl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group;
• a heteroaryl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group;
• a cycloalkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group;
• or an aralkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group,
• R6 is a carbamoyl group optionally substituted by one or two alkyl groups having 1 to 6 carbon atoms wherein the two alkyl groups having 1 to 6 carbon atoms in combination optionally form a ring containing the nitrogen atom, and the methylene group of the ring is optionally replaced by an oxygen atom;
• an alkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group;
• or a carboxyl group, and
• the carbon atom marked with * is an asymmetric carbon atom,
• which comprises subjecting a carbonyl compound represented by the formula (6):
• wherein R5 and R6 are as defined above,
• to asymmetric transfer hydrogenation in the presence of
• a chiral iridium aqua complex represented by the formula (5):
• wherein
• R7 is an aryl group substituted by haloalkyl group(s) having 1 to 6 carbon atoms,
• R8 and R9 are the same or different and each is an aralkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a nitro group, a carboxyl group and a cyano group, or an alkyl group or a hydrogen atom,
• X is a monovalent or divalent anion, and
• n is 2 when X is a monovalent anion, or n is 1 when X is a divalent anion.