Patent ID: 7705165

Claim:
A method for producing an optically active cyclopropanecarboxylate compound represented by the formula (5): wherein R 6 , R 7 , R 8 and R 9 are the same or different, and independently represent a hydrogen atom; a halogen atom; a C1-C6 alkyl group which is optionally substituted with a halogen atom or atoms, a C1-C6 alkoxy group or groups, a C7-C12 aralkyloxy group or groups, a C2-C10 acyloxy group or groups, a C2-C7 alkoxycarbonyloxy group or groups, or a C7-C11 aryloxycarbonyloxy group or groups; a C1-C6 alkenyl group which is optionally substituted with a halogen atom or atoms or a C2-C7 alkoxycarbonyl group or groups; a C6-C10 aryl group which is optionally substituted with a C1-C6 alkoxy group or groups; a C7-C12 aralkyl group which is optionally substituted with a C1-C6 alkoxy group or groups; or a C2-C7 alkoxycarbonyl group which is optionally substituted with a halogen atom or atoms, a C1-C6 alkoxy group or groups, a C7-C12 aralkyloxy group or groups, a C2-C10 acyloxy group or groups, a C2-C7 alkoxycarbonyloxy group or groups, or a C7-C11 aryloxycarbonyloxy group or groups; provided that, when R 6 and R 8 represent the same, R 6 and R 7 represent different groups each other; and R 10 represents a C1-C6 alkyl group, which comprises reacting an olefin represented by the formula (3): wherein R 6 , R 7 , R 8 and R 9 are as described above, with a diazoacetic acid ester represented by the formula (4): N 2 CHCO 2 R 10 (4) wherein R 10 is as described above, in the presence of an asymmetric copper complex obtained by mixing (A) at least one monovalent or divalent copper compound, (B) at least one optically active bisoxazoline compound represented by the formula (1): wherein R 1 and R 2 are the same or different, and independently represent a hydrogen atom; a C1- C6 alkyl group; a phenyl group which is optionally substituted with a C1-C6 alkyl group or groups, or a C1-C6 alkoxy group or groups; or a C7-C12 aralkyl group which is optionally substituted with a C1-C6 alkoxy group or groups, or R 1 and R 2 are bonded together to represent a C2-C6 polymethylene group, R 3 represents a methyl group; an isopropyl group; an isobutyl group; a tert-butyl group; a 1-naphthyl group; a 2-naphthyl group; a phenyl group which is optionally substituted with a C1-C6 alkyl group or groups, or a C1-C6 alkoxy group or groups; or a C7-C12 aralkyl group which is optionally substituted with a C1-C6 alkoxy group or groups, and R 4 and R 5 are the same and represent hydrogen atoms or C1-C3 alkyl groups, or R 4 and R 5 are bonded together to represent a C2-C5 polymethylene group, and (C) at least one fluorine compound represented by the formula (2): A-MF 6 (2) wherein A represents a lithium atom, a sodium atom, a potassium atom, a silver atom or a trityl group, and M represents a phosphorous, arsenic or antimony atom.