Process for preparing optically active cyclic amines

A process for preparing optically active cyclic amines of the formula (I) or salts thereof

• in which
• A, together with the carbon atoms designated with an asterisk (*) in each case, is a carbocyclic or heterocyclic, saturated or unsaturated, nonaromatic ring which has from 3 to 30 ring atoms, and may be further substituted in addition to the R1 and NH—R0 radicals,
• R0, independently of R, is a (C1-C6)alkyl, (C3-C6)alkenyl or (C3-C1)alkynyl radical, where each of the three latter radicals may be unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)oyloxy, (C1-C4)haloalkanoyloxy, aryl, aryloxy, amyl, aroyloxy and heterocyclyl, where each of the latter 5 radicals is unsubstituted or substituted, or
• (C3-C9)cycloalkyl, (C4-C9)cycloalkenyl, aryl or heterocyclyl, where each of the latter 4 radicals is unsubstituted or substituted,
• R, independently of R0, is
• (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, where each of the three latter radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, aryl which is unsubstituted or substituted, and heteroaryl which is unsubstituted or substituted, or
• aryl which is unsubstituted or substituted, or
• heteroaryl which is unsubstituted or substituted,
• or
• R0 and A form a ring B1 and, together with the NH group and the carbon atom which is designated with an asterisk (*) and is bonded to the NH group, are a heterocyclic ring which has from 4 to 30 ring atoms, and is optionally additionally further substituted and which optionally contains 1 or 2 further heteroatoms from the group of N, O and S,
• or
• R and A form a ring B2 and, together with the carbon atom which is designated with an asterisk (*) and is bonded to R, are a carbocyclic or heterocyclic ring which has from 3 to 30 ring atoms, and is optionally additionally further substituted, and which, in the case of a heterocyclic ring, contains 1, 2 or 3 further heteroatoms from the group of N, O and S,
• or
• R0 and R form a ring B3 and, together with the NH group and the carbon atoms designated with an asterisk (*) in each case, are a heterocyclic ring which has from 4 to 30 ring atoms, and is optionally additionally further substituted and which optionally contains 1 or 2 further heteroatoms from the group of N, O and S,
• or
• R0 and R and, if appropriate, A may simultaneously form two or more of the rings B1, B2 and B3 mentioned,
• where R and the NH—R0 group on the two ring carbon atoms marked with an asterisk (*) in each case are arranged in cis arrangement to one another and the stereochemical configuration on these carbon atoms is different from the racemic configuration, which comprises converting an imine of the formula (II) or a salt thereof
• where A, R0 and R are each as defined in formula (I) and the compound of the formula (II), with regard to the ring carbon atom marked with an asterisk (*), is present in the form of a racemic mixture or in the form of a mixture with any other isomeric ratio of the stereoisomers in question,
• in the presence of hydrogen or a hydrogen donor and a nonenzymatic catalyst which comprises a catalytically active optically active complex of one or more transition metals from the group of ruthenium, rhodium, palladium, iridium, osmium, platinum, iron, nickel and samarium, with organic ligands, to the compound of the formula (I).