Optically active halohydrin derivative and process for producing optically active epoxy alcohol derivative from the same

A process for producing an optically active halohydrin derivative represented by general formula (6):

• (wherein X2 represents a halogen atom;
• R3 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted acyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heterocycle;
• Ar2 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
• and each of *3 and *4 each represents an asymmetric carbon), the process comprising:
• allowing an optically active haloketone derivative represented by general formula (4):
• (wherein x2, R3, and *3 are the same as above) to react with a compound represented by general formula (5):
• Ar2M2 (5)
• (wherein Ar2 is the same as above;
• and M2 represents an alkali metal or a halogenated alkaline-earth metal).

A process for producing an optically active halo diol derivative represented by general formula (13):

• (wherein X2 represents a halogen atom;
• Ar2 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
• and each of *3 and *4 represents an asymmetric carbon), the process comprising:
• subjecting a compound represented by general formula (6a):
• (wherein X2, Ar2, *3, and *4 are the same as above;
• and R9 represents a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted heterocycle) to at least one treatment selected from acid treatment, fluorine compound treatment, and hydrogenolysis.

A process for producing an optically active epoxide derivative represented by general formula (16):

• (wherein Ar2 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
• and each of *7 and *8 represents an asymmetric carbon), the process comprising:
• allowing an optically active halo diol derivative represented by general formula (13):
• (wherein X2 represents a halogen atom;
• Ar2 is the same as above;
• and each of *3 and *4 represents an asymmetric carbon) to react with a compound represented by general formula (15):
• wherein R11 represents a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms).