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1. A method for producing an optically active isopulegol represented by the following general formula (3), the method comprising asymmetrically isomerizing a compound represented by the following general formula (1) in the presence of a ruthenium catalyst and a base, thereby giving an optically active citronellal represented by the following general formula (2) and selectively cyclizing the optically active citronellal represented by the general formula (2) in the presence of an aluminum catalyst,
wherein the aluminum catalyst is one obtained by reacting a hydroxy compound represented by the following general formula (5) or a hydroxy compound represented by the following general formula (6) and at least one aluminum compound selected from an alkylaluminum compound represented by the following general formula (7), a hydride aluminum compound represented by the following general formula (8), a linear aluminoxane represented by the following general formula (9) and a cyclic aluminoxane represented by the following general formula (10): wherein the wavy line represents an (E) form and/or (Z) form of the double bond, wherein * indicates an asymmetric carbon atom, wherein * indicates an asymmetric carbon atom, wherein R1 and R5 each independently represents an aryl group having from 6 to 15 carbon atoms, which may have a substituent, a heteroaryl group having from 4 to 15 carbon atoms, which may have a substituent, or a cyclic alkyl group having from 3 to 15 carbon atoms, which may have a substituent; R2, R3 and R4 each independently represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, an alkoxy group having from 1 to 8 carbon atoms, an aryl group having from 6 to 15 carbon atoms, which may have a substituent, a perfluoroalkyl group having from 1 to 4 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a halogen atom, an organosilyl group, a dialkylamino group having from 1 to 4 carbon atoms, a thioalkoxy group having from 1 to 4 carbon atoms, a nitro group, or a polymer chain, wherein R6, R9, R10 and R13 each independently represents an aryl group having from 6 to 15 carbon atoms, which may have a substituent, a heteroaryl group having from 4 to 15 carbon atoms, which may have a substituent, or a cyclic alkyl group having from 3 to 15 carbon atoms, which may have a substituent; R7, R8, R11 and R12 each independently represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, an alkoxy group having from 1 to 8 carbon atoms, an aryl group having from 6 to 15 carbon atoms, which may have a substituent, a perfluoroalkyl group having from 1 to 4 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a halogen atom, an organosilyl group, a dialkylamino group having from 1 to 4 carbon atoms, a thioalkoxy group having from 1 to 4 carbon atoms, a nitro group, or a polymer chain, A represents (i) a single bond, (ii) a linear, branched or cyclic alkylene group having from 1 to 25 carbon atoms, which may have one or more of a substituent and an unsaturated bond, (iii) an arylene group having from 6 to 15 carbon atoms, which may have a substituent, (iv) a heteroarylene group having from 2 to 15 carbon atoms, which may have a substituent, or (v) a functional group or a hetero element, which is selected from the group consisting of —O—, —S—, —N(R14)—, —S(O)—, —C(O)—, —S(O)2—, —P(R14)—, —(R14)P(O)— and —Si(R15R16)—; R14 to R16 each independently represents an alkyl group having from 1 to 6 carbon atoms, a cyclic alkyl group having from 5 to 8 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, which may have a substituent, or an aryl group having from 6 to 10 carbon atoms, which may have a substituent,
AlHk(Lg)3-k (7) wherein Al represents aluminum, Lg represents a branched or linear alkyl group having from 1 to 8 carbon atoms, a cyclic alkyl group having from 5 to 8 carbon atoms, or an aralkyl group having from 7 to 12 carbon atoms, which may have a substituent; and k indicates an integer of from 0 to 3,
MAlH4 (8) wherein Al represents aluminum, M represents lithium, sodium or potassium, wherein Al represents aluminum, R17 represents a branched or linear alkyl group having from 1 to 8 carbon atoms, a cyclic alkyl group having from 5 to 8 carbon atoms, or an aralkyl group having from 7 to 12 carbon atoms, which may have a substituent, and a plurality of R17 may be the same or different; and 1 indicates an integer of from 0 to 40, wherein Al represents aluminum, R18 represents a branched or linear alkyl group having from 1 to 8 carbon atoms, a cyclic alkyl group having from 5 to 8 carbon atoms, or an aralkyl group having from 7 to 12 carbon atoms, which may have a substituent; and j indicates an integer of from 0 to 40. |
