Optically active bisoxazoline compounds, process for production of the same and use thereof

A process for producing the optically active diamide compound represented by the formula (2):

• wherein R1 and R2 are the same, and each represent a C1-6 alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R1 and R2 are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring;
• R3 represents a substituted or unsubstituted naphthyl group;
• R4 and R5 are the same and each represents a hydrogen atom or a C1-6 alkyl group, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms;
• and * represents an asymmetric center, which comprises reacting an optically active amino alcohol represented by the formula (3):
• wherein R1, R2, R3, and * are as defined in the formula (2) with a malonic acid compound represented by the formula (4):
• wherein R4 and R5 are as defined in the formula (2);
• and Z represents an alkoxy group or a halogen atom.

An asymmetric copper complex produced from a copper compound and the optically active bisoxazoline compound represented by the formula (1):

• wherein R1 and R2 are the same, and each represents a C1-6 alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R1 and R2 are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring;
• R3 represents a substituted or unsubstituted naphthyl group;
• R4 and R5 are the same and each represents a hydrogen atom or a C1-6 alkyl group, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms;
• and * represents an asymmetric center.

A process for producing an amino alcohol represented by the formula (40):

• wherein R31, R32, R33, and R34 are the same or different, and independently represent a hydrogen atom, a C1-6 alkyl group, or a C1-6 alkoxy group;
• R35 represents a C1-6 alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted aralkyl group or two R35 bonded to the same carbon atom are bonded together with the carbon atom to form a ring, which comprises the following steps (A) to (D):
• (A) reacting a naphthylglycine compound represented by the formula (41):
• wherein R31, R32, R33, and R34 are the same or different and independently represent a hydrogen atom, a C1-6 alkyl group, or a C1-6 alkoxy group, with a chlorinating agent and an alcohol represented by the formula (42):
• R9OH (42)
• wherein R9 represents a C1-6 alkyl group, to obtain an amino acid ester hydrochloride represented by the formula (43):
• wherein R31, R32, R33, R34 and R9 are as described above,
• (B) reacting the amino acid ester hydrochloride represented by the formula (43) obtained in the above step (A) with a compound represented by the formula (44):
• (CnF2n+1CO)2O (44)
• wherein n represents 1, 2 or 3, or the formula (45):
• CnF2n+1COX (45)
• wherein n is as described above;
• and X represents a chlorine atom, a bromine atom, or an iodine atom, in the presence of a tertiary amine to obtain a compound represented by the formula (46):
• wherein R31, R32, R33, R34, R9 and n are as described above,
• (C) reacting the compound (46) obtained in the above step (B) with a compound represented by the formula (47):
• R35MgX′ (47)
• wherein R35 represents a C1-6 alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group;
• and X′ represents a halogen atom, or a compound represented by the formula (48):
• X′—Mg—R35′—Mg—X′ (48)
• wherein R35′ represents a C2-6 alkylene group and X′ is as defined above to obtain a compound represented by the formula (49):
• wherein R31, R32, R33, R34, R35 and n are as defined above, and
• (D) reacting the compound (49) obtained in the above step (C) with a base.