Use of ferrocenyl ligands for catalytic, enantioselective hydrogenation

A method for the homogeneous, catalytic, enantioselective hydrogenation of C═C and C═N double bonds comprising using an enantiomer-enriched ligand of general formula I, or salt thereof

• in which
• R1, R2, R3 signify, independently of each other, H, NR6R7, SR6, (C1-C8)-alkyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, (C1-C8)acyloxy, which are linear or branched and may be substituted singly or multiply with halogens, with groups containing N, O, P, S atoms,
• (C3-C7)-cycloalkyl, which may be substituted singly or multiply with linear or branched (C1-C8)-alkyl, which may be optionally substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms and/or may contain heteroatoms such as N, O, P, S in the ring such as 1-, 2-, 3-, 4-piperidyl, such as 1-, 2-, 3-pyrrolidinyl, 2-, 3-tetrahydrofuryl, 2-, 3-, 4-morpholinyl,
• (C6-C18)-aryl, such as phenyl, 1-, 2-naphthyl or anthryl, (C6-C18)-aralkyl, such as benzyl or 1,1-, 1,2-phenethyl, (C5-C18)-heteroaryl, such as 2-, 3-furyl, 2-, 3-pyrrolyl, 2-, 3-, 4-pyridyl,
• (C6-C18)-heteroaralkyl, such as furfuryl, pyrrolylmethyl, pyridylmethyl, 1-, 2-furylethyl, 1-, 2-pyrrolylethyl, 1-, 2-pyridylethyl, which aryl, aralkyl, heteroaryl or heteroaralkyl groups may optionally be substituted singly or multiply with linear or branched (C1-C8)-alkyl, (C1-C8)-acyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms,
• or R1 and R2 are joined in a (C3-C7)-carbocycle which can be substituted singly or multiply with linear or branched (C1-C8)-alkyl, (C1-C8)-acyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may optionally be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms and/or can contain heteroatoms such as N, O, P, S in the ring,
• R4 signifies (C1-C8)-alkyl, (C6-C18)-aryl, such as phenyl, 1-, 2-naphthyl, 2,2′-biphenyl or anthryl,1-pyrrolyl, and the just-cited groups may be optionally substituted with linear or branched (C1-C8)-alkyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms,
• (C3-C7)-cycloalkyl, which may be singly or multiply substituted with linear or branched (C1-C8)-alkyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which can be optionally substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms and/or can contain heteroatoms such as N, O, P, S in the ring,
• R5 signifies H or a group B—X—Z in which B is a residue selected from the group consisting of CR82, NR8, O, S, and SiR82, X is a spacer selected from the group consisting of 1,4′-biphenyl, 1-, 2-ethylene, 1-, 3-propylene, and PEG-(2-10) and Z is a group bound to a polymer via a functional group selected from O—, NH—, COO—, CONH—, ethenyl-, NHCONH—, OCONH— and NHCOO—,
• or the groups R5 of the two cyclopentadienyl rings are connected to each other via an α, ω-(C2-C4)-alkylene bridge,
• R6, R7 signify, independently of one another, H, (C1-C8)-alkyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, (C1-C8)-acyl, which are linear or branched and may be singly or multiply substituted with halogens, with groups containing N, O, P, S atoms,
• (C3-C7)-cycloalkyl, which may be substituted singly or multiply with linear or branched (C1-C8)-alkyl, (C1-C8)-acyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may optionally be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms and/or may contain heteroatoms such as N, O, P, S in the ring such as 1-, 2-, 3-, 4-piperidyl, such as 1,2-, 3-pyrrolidinyl, 2-, 3-tetrahydrofuryl, 2-, 3-, 4-morpholinyl, (C6-C18)-aryl, such as phenyl, 1-, 2-naphthyl or anthryl, (C6-C18)-aralkyl, such as benzyl or 1,1-, 1,2-phenethyl, (C5-C18)-heteroaryl, such as 2-, 3-furyl, 2-, 3-pyrrolyl, 2-, 3-, 4-pyridyl, (C6-C18)-heteroaralkyl, such as furfuryl, pyrrolylmethyl, pyridylmethyl, 1-, 2-furylethyl, 1-, 2-pyrrolylethyl, 1-, 2-pyridylethyl, which aryl, aralkyl, heteroaryl or heteroaralkyl groups may optionally be substituted singly or multiply with linear or branched (C1-C8)-alkyl, (C1-C8)-acyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms,
• or R6 and R7 are joined in a (C3-C7) carbocycle, which may be substituted singly or multiply with linear or branched (C1-C8)-alkyl, (C1-C8)-acyl, (C1-C8)-alkoxy, (C2-C8)-alkoxyalkyl, which may optionally be substituted singly or multiply with halogens, groups containing N, O, P, S atoms, with halogens, with groups containing N, O, P, S atoms, and/or can contain heteroatoms such as N, O, P, S in the ring, and
• R8 signifies H, (C1-C8)-alkyl.