Patent ID: 8153830

Claim:
A method of producing an asymmetric copper complex crystal comprising reacting an optically active salicylidene amino alcohol compound of the formula (1): wherein, R 1 represents an alkyl group, aryl group or aralkyl group, R 2 represents an optionally substituted alkyl group or optionally substituted phenyl group, R 3 and R 4 are the same or mutually different and represent a hydrogen atom, halogen atom, nitro group, alkyl group, fluoroalkyl group, alkoxy group, alkoxycarbonyl group, trialkylsilyl group or cyano group, and * represents that the carbon atom is an optically active point with a copper compound, then, performing a crystallization treatment in the presence of an alcohol solvent, wherein the optically active salicylidene amino alcohol compound of the formula (1) is a compound obtained by reacting an optically active amino alcohol compound of the formula (2): with a salicylaldehyde compound of the formula (3): wherein the optically active amino alcohol compound of the formula (2) is a compound obtained by reacting an optically active amino acid ester compound of the formula (4): wherein, R 1 and * represent the same meanings as described above, and R 5 represents an optionally substituted alkyl group or optionally substituted phenyl group with a Grignard compound of the formula (5): R 2 —MgX (5) wherein R 2 represents the same meanings as described above, and X represents a halogen atom, and wherein the optically active amino acid ester compound of the formula (4) is a compound obtained by treating an addition salt of the optically active amino acid ester compound and an acid with a tertiary amine compound base.