An aluminum catalyst is obtained by reacting at least one compound of a specific alkylaluminum compound and a specific hydridoaluminum compound with a specific hydroxy compound. The specific hydroxyl compound is a specific 2-cycloalkyl-6-arylphenol or a specific di(2-cycloalkyl-6-arylphenol). A method for producing isopulegol or optically active isopulegol includes selectively cyclizing citronellal using the aluminum catalyst.

A method for producing an optically active α-trifluoromethyl-β-amino acid derivative, the method including: allowing a compound represented by the following General Formula (1) and a compound represented by the following General Formula (2) to react in the presence of a copper-optically active phosphine complex obtained from a copper compound and an optically active phosphine compound, to thereby obtain an optically active α-trifluoromethyl-β-amino acid derivative represented by the following General Formula (3):

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A method for preparing chiral γ-secondary amino alcohol includes: adding into a solvent an acid addition salt of β-secondary amino ketone represented by general formula (1), an alkali, a metal salt additive and a diphosphine-rhodium complex, so as to carry out a reaction in a hydrogen atmosphere and obtain a chiral γ-secondary amino alcohol compound represented by general formula (2). In general formula (2), Ar represents an aryl group with or without substituent group(s), R represents an alkyl group or an aralkyl group, and HY represents an acid. The synthesis scheme has a simple process, the metal salt additive remarkably improves the effect of a rhodium-catalyzed asymmetric hydrogenation technology, and accordingly, the reaction yield and the optical purity of a product are improved, the production process is simplified, production costs are reduced, and the synthesis scheme is highly suitable for mass industrial production.

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A ligand having the structure or its enantiomer; (I) wherein: each one of R.sub.a, R.sub.b, R.sub.c and R.sub.d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH.sub.2NH; *CH(CH.sub.3)NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of R.sub.a, R.sub.b, R.sub.c and R.sub.d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH.sub.2NH; *CH(CH.sub.3)NH(C*,R); and *CH(CH.sub.3)NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe. ##STR00001##

A ligand having the structure or its enantiomer; (I) wherein: each one of R.sub.a, R.sub.b, R.sub.c and R.sub.d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH.sub.2NH; *CH(CH.sub.3)NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of R.sub.a, R.sub.b, R.sub.c and R.sub.d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH.sub.2NH; *CH(CH.sub.3)NH(C*,R); and *CH(CH.sub.3)NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe. ##STR00001##

The present invention pertains to a method for producing an optically active compound which includes a step for reducing an imino group of an imine compound or a step for reducing an unsaturated bond of a heterocyclic compound, while in the presence of hydrogen gas as a hydrogen donor and one or more types of complexes selected from a group consisting of a complex represented by general formula (1), a complex represented by general formula (2), a complex represented by general formula (3), and a complex represented by general formula (4) (the general formulas (1)-(4) are as stipulated by claim 1).

The present invention pertains to a method for producing an optically active compound which includes a step for reducing an imino group of an imine compound or a step for reducing an unsaturated bond of a heterocyclic compound, while in the presence of hydrogen gas as a hydrogen donor and one or more types of complexes selected from a group consisting of a complex represented by general formula (1), a complex represented by general formula (2), a complex represented by general formula (3), and a complex represented by general formula (4) (the general formulas (1)-(4) are as stipulated by claim 1).

This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M.sup.m+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R.sup.10a, R.sup.10b, R.sup.10c, R.sup.10d, R.sup.10a′, R.sup.10b′, R.sup.10c′, R.sup.10d′, Z and Z′ have the meanings as defined in the description.

This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M.sup.m+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R.sup.10a, R.sup.10b, R.sup.10c, R.sup.10d, R.sup.10a′, R.sup.10b′, R.sup.10c′, R.sup.10d′, Z and Z′ have the meanings as defined in the description.

The present invention relates to a process for the preparation of a compound of formula (I) wherein A.sub.1 and A.sub.2 are C—H, or one of A.sub.1 and A.sub.2 is C—H and the other is N; R.sub.1 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl or C.sub.3-C.sub.6cycloalkyl; each R.sub.2 is independently bromo, chloro, fluoro or trifluoromethyl; R.sub.3 is hydrogen; R.sub.4 is hydrogen, halogen, methyl, halomethyl or cyano; or R.sub.3 and R.sub.4 together form a bridging 1,3-butadiene group; R.sub.5 is chlorodifluoro-methyl or trifluoromethyl; n is 2 or 3; by reacting a compound of formula (II) wherein A.sub.1, A.sub.2, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n is as defined under formula (I) above, with hydroxylamine, a base and a chiral catalyst, characterized in that the chiral catalyst is a dimeric chiral catalyst of formula (III) wherein R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and X are as defmed in claim 1.

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