Method for producing optically active alcohol compound

A method for producing an optically active alcohol compound comprising reacting a cyclic ether compound with a phenol compound in the presence of an asymmetric complex obtained by reacting an optically active metal complex represented by the formula (1):

• wherein R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, a substituted or unsubstituted aryl group, an aralkyl group, a hydroxyl group, a nitro group, an amino group, a carbamoyl group, a carboxyl group, or a silyl group;
• or two adjacent groups of R1, R2, R3, R4, R5, R6, R7 and R8 are combined together to represent a naphthalene ring by forming a ring together with a benzene ring to which they are attached;
• one of R9 and R10 is a hydrogen group and the other is a phenyl group or a naphthyl group optionally substituted with at least one selected from the group consisting of a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom and a halogen atom;
• or either one pair of R9 and R10 attached to the different carbon atoms are combined together at their ends to form a tetramethylene group and the other pair are hydrogen atoms;
• Q represents a single bond or a C1-C4 alkylene group;
• or Q is combined with R9 and R10 to represent a 1,1′-binaphthyl group attached to the nitrogen atoms at 2 and 2′ positions;
• M represents a metal ion;
• and when an ionic valency of the metal ion is same as a coordination number of a ligand, A is nonexistent, and when the above-mentioned ionic valency is different from the coordination number, and A represents a counter ion or a ligand, with a metal sulfonate.