Process for producing optically active halohydrin compound

A process of preparing an optically active halohydrin compound represented by general formula (3), comprising

• reducing an α-haloketone compound represented by general formula (1) by asymmetric hydrogen transfer in the presence of a group 9 transition metal compound having a substituted or unsubstituted cyclopentadienyl group and an optically active diamine compound represented by general formula (2);
• wherein X represents a halogen atom;
• Y represents an aromatic hydrocarbon group, an aromatic heterocyclic group, an unsaturated hydrocarbon group or
• wherein Ra and Rb each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, in which the alkyl, aryl and aralkyl group may contain a hetero atom in the carbon skeleton thereof;
• and Y1 represents an amino group, a protected amino group, a hydroxyl group or a protected hydroxyl group;
• wherein R1 represents an alkyl group, a fluoroalkyl group or a substituted or unsubstituted phenyl group;
• R2 and R3, which may be the same or different, each represent a substituted or unsubstituted phenyl group or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or R2 and R3 are taken together to form a ring;
• * indicates an asymmetric carbon;
• k represents an integer of 0 to 3;
• and the steric configuration is (S,S) or (R,R);
• wherein X and Y are as defined above, and * indicates an asymmetric carbon.