Process for producing optically active cis-silyl olefin oxide compound

A production method of an optically active cis-silylolefin oxide compound of Formula (11):

• (where R5 is a hydrogen atom, a C1-22 alkyl group, a C1-4 alkoxy group, or a C6-10 aryl group (the aryl group is unsubstituted or is substituted with a halogen atom, a C1-4 alkyl group, a C6-10 aryl group (the aryl group is unsubstituted or is substituted with a halogen atom, a C1-4 alkyl group or a C1-4 alkoxy group) or a C1-4 alkoxy group),
• R6, R7 and R8 are each independently a hydrogen atom, a C1-22 alkyl group or a C6-10 aryl group (the aryl group is unsubstituted or is substituted with a halogen atom, a C1-4 alkyl group or a C1-4 alkoxy group),
• R9 and R10 are each independently a hydrogen atom, a C1-6 alkyl group (the alkyl group is optionally substituted with a halogen atom, a C1-6 alkoxy group (the alkoxy group is optionally substituted with a halogen atom) or a hydroxy group) or a C6-14 aryl group (the aryl group is optionally substituted with a halogen atom, a hydroxy group, a nitro group, a cyano group, a C1-6 alkyl group (the alkyl group is optionally substituted with a halogen atom, a C1-6 alkoxy group (the alkoxy group is optionally substituted with a halogen atom) or a hydroxy group) or a C1-6 alkoxy group (the alkoxy group is optionally substituted with a halogen atom)),
• n is an integer of 0 to 3, and
• the absolute configuration of the carbon atoms marked with “*” means (R) or
• characterized by subjecting a cis-silylolefin compound of Formula (10):
• (where R5, R6, R7, R8, R9, R10 and n are the same as those defined above) to an asymmetric epoxidation with an oxidant using as a catalyst, an optically active titanium complex of any one of Formula (1), Formula (1′), Formula (2), Formula (2′), Formula (3), Formula (3′), Formula (4) and Formula (4′):
• (where in Formula (1), Formula (1′), Formula (2), Formula (2′), Formula (3), Formula (3′), Formula (4) and Formula (4′), R1 is a hydrogen atom, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a C6-12 aryloxy group or a C6-22 aryl group (the aryl group is substituted with a C1-4 alkyl group (the alkyl group is optionally substituted with a halogen atom), a C1-7 alkoxy group or a benzyloxy group, and is optically active or optically inactive);
• R2 is a hydrogen atom, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a C6-12 aryloxy group or a C6-18 aryl group;
• R3 is a C1-4 alkyl group, a C6-18 aryl group, or a C3-5 divalent group when two R3s together form a ring;
• R4s are each independently a hydrogen atom, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, a nitro group or a cyano group;
• and M is TiJ1J2 (in TiJ1J2:
• Ti is a titanium atom;
• J1 and J2 are each independently a halogen atom or C1-4 alkoxide, J1 and J2 together are an oxygen atom, or J1 and J2 together form a ring to form a binuclear complex of Formula (5):
• (where a partial structural formula O-E-O in Formula (5) is a formula of any one of Formula (6), Formula (6′), Formula (7), Formula (7′), Formula (8), Formula (8′), Formula (9) and Formula (9′):
• (where R1, R2, R3 and R4 in Formula (6), Formula (6′), Formula (7), Formula (7′), Formula (8), Formula (8′), Formula (9) and Formula (9′) are the same as those defined above, and at this time, two partial structures O-E-O in Formula (5) are the same as each other))).