Patent ID: 6670500
Filing Date: 2003-12-30
Classification: C07B,C07C

Abstract:
A method for producing an optically active cyclopropanecarboxylic acid ester of formula (4): wherein R3, R4, R5, R6 and R7 are as defined below,which comprises reacting a prochiral olefin of formula (5): wherein R3, R4, R5 and R6 are as defined below, with a diazoacetic acid ester of formula (6): N2CHCO2R7â€ƒâ€ƒ(6), wherein R7 is as defined below, in the presence of a chiral copper complex obtained by contacting a monovalent or divalent cooper compound with an optically active salicylideneaminoalcohol compound of formula (1): wherein R1 representsan alkyl group which may be substituted with a group selected from an alkoxy group, an aralkyloxy group, an aryloxy group and cycloalkoxy group, an aralkyl, aryl or cycloalkyl group all of which may be substituted with a group selected from an alkyl group, an alkoxy group, an aralkyloxy group, an aryloxy group and a cycloalkoxy group, R2 represents an alkyl group, a cycloalkyl group, or an aralkyl or phenyl group which may be substituted with a group selected from an alkyl group, an alkoxy group, an aralkyloxy group, an aryloxy group and a cycloalkoxy group, wherein X1 represents a nitro group, X2 is a hydrogen atom, when X1 represents a chlorine atom, X2 is a chlorine atom, and when X1 is a hydrogen atom, X2 is a fluorine atom; and the carbon atom denoted by â€œ*â€  is an asymmetric carbon atom having either an S or R configuration, and wherein R3, R4, R5 and R6 independently represent a hydrogen atom, a halogen atom, a (C1-C8)alkyl group which may be substituted with a halogen atom or a lower alkoxy group, a (C4-C8)cycloalkyl group, an aryl group which may be substituted with a halogen atom or a lower alkoxy group, an alkoxy group, R3 and R4, or R5 and R6 together form a cycloalkylene group having 2-4 carbon atoms, provided that one of R3, R4, R5 and R6 groups represents an alkenyl group which may be substituted with a halogen atom, an alkoxy group or an alkoxy carbonyl group, of which alkoxy may be substituted with a halogen atom or atoms, and provided that when R3 and R5 are the same, R4 and R6 are not the same, and R7 represents an alkyl group having 1 to 8 carbon atoms, a benzyl group which may be optionally substituted with a cycloalkyl group, a lower alkyl group, a lower alkoxy group, a phenoxy group or a halogen atom, or a phenyl group which may be optionally substituted with a lower alkyl group, a lower alkoxy group or a phenoxy group.