IMPROVEMENT OF THE ENANTIOSELECTIVE HYDROGENATION OF 4-SUBSTITUTED 1,2-DIHYDROQUINOLINES IN THE PRESENCE OF AN IRIDIUM CHIRAL CATALYST AND AN ADDITIVE

Abstract

The invention relates to a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines comprising the enantioselective hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in the presence of a chiral iridium (P,N)-ligand catalyst and an additive.

Description

IMPROVEMENT OF THE ENANTIOSELECTIVE HYDROGENATION OF 4-SUBSTITUTED 1,2-DIHYDROQUINOLINES IN THE PRESENCE OF AN IRIDIUM CHIRAL CATALYST AND AN ADDITIVE The invention relates to a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines comprising the enantioselective hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in the presence of a chiral iridium (P,N)-ligand catalyst and an additive. It is known from document EP 0 654 464 that N-acetyl-tetrahydroquinolines can be converted into the corresponding 4-aminoindane derivatives by a rearrangement reaction. 4-Aminoindane derivatives are important intermediates for the preparation of various N-indanyl heteroaryl carboxamides with fungicidal activity (EP 0 654 464, WO 2011 / 162397, WO 2012 / 084812, WO 2015 / 197530). EP 3 103 789 discloses a method for optically resolving 1,1,3-trimethyl-4-aminoindane by converting the enantiomeric mixture into the diastereomeric salts of D-tartaric acid. (R) and (S)-1,1,3-trimethyl-4-aminoindane are obtained after separation and basification of the diastereomeric salts. This reference also discloses a method for racemizing the unwanted enantiomer, such that the method as a whole allows the conversion of the unwanted enantiomer into a desired enantiomer through several steps of a process. (R)-1,1,3-trimethyl-4-aminoindane is an important intermediate for the preparation of the fungicidal pyrazole carboxamide inpyrfluxam. A method for preparing chiral intermediates of N-indanyl heteroaryl carboxamides via asimatic synthesis is also known. WO 2015 / 141564 describes a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines, the process comprising the hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in the presence of a transition metal catalyst having an optically active ligand. The asymmetric hydrogenation of the 4-substituted NH-dihydroquinolines proceeded with moderate conversion rates (up to 62.6%) and enantioselectivity (up to 71.3% ee), whereas N-acetyl-dihydroquinolines exhibited even poorer conversion (up to 14%) and enantioselectivity (up to 31% ee). In light of the prior art described above, the present invention aims to provide a process for the preparation of optically active 4-substituted 1,2,3,4-tetrahydroquinolines, which process has advantages over prior art processes. The process must allow the desired enantiomer to be prepared with high yield and high enantiomeric purity, in a few steps, and purification is also achieved in few steps. Qfrfrenn / zznz / E / Yii The object described above was achieved through a process to prepare a compound of the formula(la)o (Ib), (la) (Ib) where R1 is selected from the group consisting of Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy- Ci-Ce-alkyl, Cs-Ce-cycloalkyl, Ce-Cu-aryl or C6-Ci4-aryl-Ci-C4alkyl, wherein the C1-Ce-alkyl, Ce-Ce-cycloalkyl and the Ci-Ce-alkoxy in the C1Ce-alkoxy- Ci-Ce-alkyl moiety are optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, C1-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the C6-C14-aryl-C1-C4-alkyl fraction in each case are either not substituted or are substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy, R2 and R3 are equal and are selected from the group consisting of hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl and Ci-Ce-alkoxy- Ci-Ce-alkyl, or R2 and R3 together with the carbon to which they are attached, form a Cs-Ce-cycloalkyl ring, R4 is hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cecycloalkyl, Cs-Ce-cycloalkyl-, Ci-C4-alkyl, C2-C6-alkenyloxy-, 9-fluororenylmethyleneoxy, Ce-Cu-aryl, Ce-Cu-aryloxy, Ce-Ci4-aryl-Ci-C4-alkyloxy or Ce-Ci4-aryl-Ci-C4-alkyl, wherein the Ce-Cu-aryl as such or as part of a compound substituent is unsubstituted or is substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, n is 0,1,2,3 or 4, each R5 substituent, if present, is independently selected from the group formed by halogen, Oi-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, hydroxyl, amino and —C(=O)— Oi-Ce-alkyl, comprising the enantioselective hydrogenation of a compound of formula (II) Qbhrnn / 77n7 / E / Yl· (II) wherein the substituents R1, R2, R3, R4, R5 and the integer n are each as defined for the compound of formula (a) or (Ib), in the presence of a chiral iridium catalyst, characterized in that the chiral iridium catalyst comprises a chiral ligand of formula (Illa), (Hlb), (IVa), (IVb), (IXa) or (IXb) where R6, R7 and R8 are selected independently of each other from the group consisting of hydrogen, halogen, C1-Ce-alkyl, C1-Ce-haloalkyl, C1-Ce-alkoxy, C2-C6-alkenyl, C2-C6-alkylyne, C3-C7-cycloalkyl, C3-C7-cycloalkyl, C1-C4-alkyl, Ce-Cu-aryl and Ce-C14-aryl-C1-C4-alkyl, wherein the C1-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl and the C3-C7-cycloalkyl in the C1-C2-cycloalkyl-C1-C4-alkyl moiety are optionally replaced by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy and Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-C14-aryl in the Ce-Cu-aryl-C1-C4-alkyl moiety are optionally substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, Ci-C4-haloalkoxy and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five C1Ce-alkyl substituents,R9 and R10 are selected independently of each other from the group consisting of C1Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxy, di(Ci-Cealkyl)amino, C3-Ci2-cycloalkyl, C3-Ci2-cycloalkyl-Ci-C4-alkyl, Ce-Quaryl, C6-Ci4-aryloxy and Ce-Quaryl-Ci-C4-alkyl, wherein the Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy and di(Ci-Ce-alkyl)amino are optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, C1-C4-alkoxy-, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents independently selected from each other from halogen, C4-alkyl, C4-alkoxy, C4-haloalkyl and C1-C4-haloalkoxy, and wherein the Ce-Cu-aryl, Ce-Cu-aryloxy and C3-C12-cycloalkyl, in each case either as such or as part of a compound substituent, are optionally substituted by one to five substituents selected from the group consisting of halogen, C4-alkyl,Ci-C4-haloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is either unsubstituted or substituted by one to five Ci-C4-alkyl substituents or, R9 and rio jurit0 with the phosphorus atom to which they are attached, form a phospholane ring, which can be substituted by one or two Ci-Ce-alkyl groups, or R9 and R10 together form R13 R14 and R15 where the bonds identified by xey are directly attached to the phosphorus atom, pyq are selected independently of each other from 0,1 and 2, R11 and R12 are independently selected from Ci-C4-alkyl and phenyl, which can be substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-alkoxy and phenyl, which can be substituted by one or two Ci-C4-alkyl substituents, is 1 or 2, is where the bond identified by is directly attached to the phosphorus atom and where the bond identified by “# is directly attached to the deoxazoline moiety, is Ci-Ce-alkyl, Ci-Ce-haloalkyl, Os-C12-cycloalkyl, C3-C12-cycloalkyl, Ci-C4-alkyl, Ci-C4-alkyl-C3-C7-cycloalkyl, Ce-Cu-aryl, or Ce-Cu-aryl, Ci-C4-alkyl, where the Ce-Cu-aryl and the Ce-Cu-aryl in the C6-C14-aryl-C14-alkyl moiety in each case are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, are selected independently of each other from the group consisting of hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C3-Ci2-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-Cs-Cy-cycloalkyl, Ce-Cu-aryl and C6-Ci4-aryl-Ci-C4-alkyl,where the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl fraction are in each case either not substituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or, R14 and R15 together with the carbon to which they are attached, form a Cs-Ce-cycloalkyl ring, R16 and R17 are selected independently of each other from the group consisting of C1-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-Ce-alkoxy, di(C1-Ce-alkylamino, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C4-alkyl, C1-Quaryl, C6-C14-aryloxy and C6-C14-aryl-C1-C4-alkyl, wherein the C1-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-Ce-cycloalkyl and di(C1-Ce-alkyl)amino are optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, C1-C14-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents independently selected from each other of halogen, Ci-C4-alkyl, phenyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, and Ci-C4-haloalkoxy, and wherein Ce-Cu-aryl, Ce-Cu-aryl in Ce-Cu-aryl- Ci-C4-alkyl, CeCu-aryloxy and C3-C12-cycloalkyl, in each case either as such or as part of a compound substituent,are optionally replaced by one to five substituents selected from the group consisting of halogen, C1-C4 alkyl, phenyl, C4-haloalkyl, C4-alkoxy and C4-haloalkoxy, or, R16 and R17 together with the phosphorus atom to which they are attached, form a phospholane ring, which can be substituted by one or two Ci-Ce-alkyl groups, or R16 and R17 together form Qbhrnn / 77n7 / E / Yl· in which the bonds identified by xey are both directly attached to the phosphorus atom, pyq are selected independently of each other from 0,1 and 2, and R11 and R12 are independently selected from C1-C4-alkyl and phenyl, which can be substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1C4-alkoxy and phenyl, which can be substituted by one or two C1-C4-alkyl substituents, R19 are selected independently from phenyl, benzyl, t-butyl, isopropib, cyclohexyl, R20s are selected independently from hydrogen, methyl, ethyl, isopropyl, R21 are selected independently from hydrogen, benzyl, methyl, ethyl R22 are independently selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, and in the presence of an additive, where the additive is selected from the group consisting of Bronsted acids, Lewis acids and mixtures thereof. It has been surprisingly shown that optically active 4-substituted 1,2,3,4-tetrahydroquinolines (Ia and Ib) can be prepared with high yields and excellent enantioselectivity by enantioselective hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines (II) in the presence of a chiral iridium (P,N)-ligand catalyst and an additive. Definitions In the definitions of the symbols indicated in the preceding formulas, collective terms were used, which are generally representative of the following substituents: Halogen: fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and most preferably fluorine or chlorine. Alkyl: saturated hydrocarbon substituents, straight-chain or branched, having 1 to 6, preferably 1 to 4 carbon atoms, for example (among others) ci-Ce-alkyl such as methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.In particular, such a group is a Ci-C4-alkyl group, for example, a methyl, ethyl, propyl, 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), or 1,1-dimethylethyl (tert-butyl) group. This definition also applies to the alkyl group as part of a substituent. Qbhrnn / zznz / E / vl· compound, for example, Cs-Ce-cycloalkyl- Ci-C4-alkyl, Ce—Ci4—aryl—Ci—C4—alkyl, etc., unless defined elsewhere. Aluenyl: Substitutes of unsaturated hydrocarbons, with straight or branched chains containing between 2 and 6, preferably 2 to 4 carbon atoms and a double bond in any position, for example (among others) Cs-Cs-alquenyl, such as vinyl, allyl, (E)-2-methylvinyl, (Z)-2methylvinyl, isopropenil, homoalyl, (E)—but—2—enil, (Z)—but—2—enil, (E)-but-1—enil, (Z)-but-l-enil, 2—metilprop—2—enil, 1—metilprop—2—enil, 2—metilprop—1—enil, (E)-1 -metilprop-1 -enil, (Z)-1metilprop-1 -enil, pent-4-enil, (E)—pent—3—enil, (Z)—pent—3— enil, (E)—pent—2—enil, (Z)-pent-2enil, (E)-pent-l-enil, (Z)-pent-l-enil, 3- methylbut—3—enil, 2—metilbut—3—enil, 1 -metilbut-3-enil, 3-metilbut-2-enil, (E)—2—metilbut—2—enil, (Z)—2—metilbut—2—enil, (E)—1—metilbut—2—enil, (Z)—1metilbut—2—enil, (E)—3—metilbut—1—enil, (Z)—3—metilbut—1—enil, (E)—2— methylbut-1-enil, (Z)—2—methylbut-1-enil, (E)—1—metilbut—1—enil, (Z)—1—metilbut—1—enil, 1,1 —dimethylprop—2—enil, 1etilprop—1—enil, 1—propylvinilo, 1- isopropylvinilo,(E)—3,3—dimethylprop—1—enyl, (Z)-3,3dimethylprop—1 —enyl, hex-5-enyl, (E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3enyl, (E)-hex-2-enyl, (Z)-enyl, (Z)-2-enyl (E)—hex—I—enyl, (Z)—hex—I—enyl, 4-methylpent-4-enyl, 3methylpent-4-enyl, 2-methylpent-4-enyl, 1- methylpent-4-enyl, 4-methylpent-3-enyl, (E)- 3methylpent-3-enyl, (E)- 3-3-enyl methylpent-3-enyl, (E)-2-methylpent-3-enyl, (Z)-2-methylpent-3-enyl, (E)-1-methylpent-3-enyl, (Z)-1-methylpent-3-enyl, (E)-4-methylpent-2-enyl, (Z)-4-methylpent-2-enyl, (E)-3-methylpent-2-enyl, (Z)—3-methylpent-2-enyl, (E)-2-methylpent-2-enyl, (Z)-2-methylpent2-enyl, (E)—1—methylpent—2—enyl, (Z)-1-methylpent-2-enyl, (E)-4-methylpent-2-enyl, (E)-4-meth-enyl, (Z)-4-meth methylpent—1 —enyl, (E)-3- methylpent—1 —enyl, (Z)-3-methylpent-1 -enyl, (E)-2-methylpent-1 -enyl, (Z)-2-methylpent-1 -enyl, (Z)—2— methylpent—1 —enyl, (E)—1 —methylpent,— (Z)-1-methylpent-1enyl, 3—ethylbut—3—enyl, 2—ethylbut—3—enyl, 1 —ethylbut—3—enyl, (E)—3—ethylbut—2—enyl, (Z)—3—ethylbut—2—enyl, (E)—2—ethylbut—2—enyl,(Z)—2—ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (Z)—1 —ethylbut—2—enyl, (E)—3—ethylbut—1 —enyl, (Z)—3—ethylbut—1 —enyl, 2—ethylbut—1—enyl, (E)-1 -ethylbut-1 -enyl, (Z)-1 -ethylbut—1 -enyl, (Z)—1 -ethylbut—1 -enyl, 2—propylpropyl—2—enyl, 2-propylpropyl, (E)—2-enyl, (Z)-1 -ethylbut—1 -enyl, 2—propylpropyl—2—enyl, (Z)—1 —ethylbut—2—enyl, 2—propylpropyl—2—enyl, (Z)—1 —ethylbut—2—enyl, (Z)—1ethylbut—2—enyl, 2—ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1—ethylbut—1—enyl, (E)—1—ethylbut—2—enyl, (Z)—1—ethylbut—2—enyl, 2—propylpropylo—2—enyl, (E)— ethylbut—1 —enyl, (E)—1 —ethylbut—2—enyl, (E)-1 -ethylbuto—2-enyl, (E)-1 -ethylbut-2-enyl, (E)-1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (Z)—1 —ethylbut— 2-enyl, (E)—1 —ethylbut— 2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut—2—enyl, (E)—1 —ethylbut-2-enyl, (E)—1 —ethylbut-2-enyl, (E)-ethylbut-1 -enyl, (E)3-ethylbut-2-enyl, (E)—ethylbut-2-enyl, (E)-1 -ethylbut (E)—2-propylprop-1 -enyl, (Z)-2-propylprop1 -enyl,(E)—1 —propylprop—1 —enyl, (Z)—1 —propylprop—1 —enyl, (E)—2— isopropylprop—1 —enyl, (Z)—2— isopropylprop—1 —enyl, (E)—1—isopropylprop—1—enyl, (Z)—1 - isopropylprop—1—enyl, 1-(1,1dimethylethyl)ethenyl, buta-1,3—dienyl, penta-1,4-dienyl, hexa-1,5—dienyl or methylhexadienyl., Qbhrnn / zznz / E / Yl· Particularly, said group is vinyl or sharp. This definition also applies to alkenyl as part of a substituent compound unless def inaned elsewhere. Alauynyl: straight-chain or branched hydrocarbyl substituents having 2 to 8, preferably 2 to 6, and more preferably 2 to 4 carbon atoms and a triple bond in any position, for example (among others) Cs-Cs-alkynyl, such as ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1-ethylbut-3-ynyl, 1 -ethylbut-2-ynyl, 1 -propylprop-2-ynyl, 1 -isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl, or 3,3-dimethylbut-1-ynyl group.In particular, this alkynyl group is ethynyl, prop-1-ynyl, or prop-2-ynyl. This definition also applies to alkynyl as part of a substituent compound unless it is defined elsewhere. Alalkylamino: monoalkylamino or dialkylamino, where monoalkylamino represents an amino radical having one alkyl residue with 1 to 4 carbon atoms bonded to the nitrogen atom. Non-limiting examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, and tert-butylamino. Where dialkylamino represents an amino radical having two independently selected alkyl residues, each with 1 to 4 carbon atoms bonded to the nitrogen atom. Non-limiting examples include N,N-dimethylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-isopropyl-N-propylamino, and N-tert-butyl-N-methylamino. Alkoxy: Saturated alkoxy substituents, straight or branched chain, having from 1 to 6, more preferably from 1 to 4 carbon atoms, for example (among others) Cl-Ce-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. This definition also applies to alkoxy as part of a substituent compound unless defined elsewhere. Cycloalkyl: mono- or polycyclic saturated hydrocarbonyl substituents having 3 to 12, preferably 3 to 8, and most preferably 3 to 6 carbon ring members, e.g. (among others) cyclopropyl, cyclopentyl, cyclohexyl, and adamantyl. This definition also applies to cycloalkyl as part of a substituent compound, e.g., Ca-Cecycloalkyl-Ci-C4-alkyl, unless defined elsewhere. Haloalauyl: straight-chain or branched alkyl substituents having 1 to 6, preferably 1 to 4 carbon atoms (as specified above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, e.g. (among others) Ci-Cs-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichlorofluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a substituent compound unless it is defined elsewhere. Haloalkenyl and haloalkynyl are defined analogously to haloalkyl except that, instead of alkyl groups, alkenyl and alkynyl groups are present as part of the substituent. Haloalkoxy: straight-chain or branched alkoxy substituents having 1 to 6, preferably 1 to 4 carbon atoms (as specified above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as stated above, e.g. (among others) Cl-Cs-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2—trichloroethoxy, pentafluoroethoxy and 1,1,1trifluoroprop-2-oxy.This definition also applies to haloalkoxy as part of a substituent compound, unless it is defined elsewhere. Aryl: mono-, bi-, or tricyclic or partially aromatic substituents having between 6 and 14 carbon atoms, for example (among others) phenyl, naphthyl, tetrahydronaphthyl, indenyl, and indanyl. Linkage to the overall superordered structure can be carried out through any possible ring member of the aryl residue. The aryl group is preferably selected from phenyl, 1-naphthyl, 2-naphthyl, 9-phenanthryl, and 9-anthracenyl. Phenyl is particularly preferred. The term “enantioselective” as used herein means that one of the two possible enantiomers of the hydrogenation product is preferentially formed, namely, the enantiomer of formula (la) or the enantiomer of formula (Ib). The “enantiomeric excess” or “ee” indicates the degree of enantioselectivity: o / major enantiomer (mol) - minor enantiomer (mol) ίππο / / o ΘΘ = ~ T ~ ; ~X 1UU / 0 major enantiomer (mol) + minor enantiomer (mol) Qfrfrrnn / zznz / B / Yi The major enantiomer can be controlled by selecting the chiral ligand, for example, by selecting the chiral ligand of formula (Illa) or the opposite enantiomer (the ligand of formula (lllb)), or by selecting respectively the chiral ligand of formula (IVa) or the opposite enantiomer (the ligand of formula (IVb)). The process according to the invention is used to prepare the compound of formula (la) or (Ib), preferably (la). The preferred compounds are those of formula (la) or (Ib), especially (la), where the substituents are defined as follows: R1 is Ci-Ce-alkyl or Ce-C14-aryl-C14-alkyl, wherein Ce-C14-aryl in the Ce-C14-aryl-C14-alkyl moiety is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy. R2 and R3 are equal and are selected from Ci-C4-alkyl, R4 is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl or benzyl, n is 0,1 or 2, each R5 substituent, if present, is selected independently of the group formed by halogen, Ci-Ce-alkyl and Ci-Ce-haloalkyl. More preferred are compounds of the formula (la) or (Ib), in particular (la), in which the substituents are defined as follows: R1es Ci-Ce-alkyl R2 and R3 are equal and are selected from Ci-C4-alkyl, R4 is Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl or benzyl, n is 0, 1 or 2, each R5 substituent, if present, is selected independently of the halogen and Ci-Ce-alkyl group. Even more preferred are compounds of the formula (la) or (Ib), in particular (la), in which the substituents are defined as follows: R1 is methyl, ethyl or n-propyl, R2 and R3 are methyl, R4 is Ci-C4-alkyl, n is 0, 1 or 2, each R5 substituent, if present, is selected independently of the halogen and Ci-Ce-alkyl group. The most preferred are compounds of the formula (la) or (Ib), in particular (la), in which the substituents are defined as follows: R1 is methyl or n-propyl, R2 and R3 are methyl, R4 is methyl, n is 0 or 1, the substituent R5, if present, is fluorine. The process according to the invention comprises the enantioselective hydrogenation of the compound of formula (II). The substituents R1, R2, R3, R4, R5 and the integer n in the compound of formula (II) are each as defined for the compound of formula (a) or (Ib). The enantioselective hydrogenation of the compound of formula (II) is carried out in the presence of an additive selected from the group consisting of Bronsted acids, Lewis acids and mixtures thereof. In a preferred embodiment of the process according to the invention, the additive is selected from the group consisting of hexafluorophosphoric acid, acetic acid, trifluoromethylsulfonic acid, water, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid, tetrafluoroboric acid diethyl ether complex, Nafion, Amberlyst, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, borane tetrahydrofuran complex, boric acid, aluminum(III) trifluoromethanesulfonate, zinc(II) trifluoromethanesulfonate, scandium(III) trifluoromethanesulfonate, aluminum(III) fluoride, titanium(IV) isopropoxide, trimethyl aluminum, trif boron fluoride, boron trifluoride complexes and mixtures thereof. Suitable boron trifluoride complexes are boron trifluoride complexes with organic solvents, such as dialkyl ethers or alcohols, and boron trifluoride complexes with organic acids, such as carboxylic acids. Preferred boron trifluoride complexes are selected from the group consisting of the boron trifluoride-diethyl ether complex, the boron trifluoride-acetic acid complex, and the boron trifluoride-n-propanol complex. In a more preferred embodiment of the process according to the invention, the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid diethyl ether complex, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes, and mixtures thereof, wherein the boron trifluoride complexes are selected Qbhrnn / zznz / E / Yl· preferably from the group formed by the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex and the boron trifluoride n-propanol complex. In a further preferred embodiment of the process according to the invention, the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, trifluorophenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes and mixtures thereof, wherein the boron trifluoride complexes are preferably selected from the group consisting of the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex and the boron trifluoride n-propanol complex. In the most preferred embodiment of the process according to the invention, the additive is selected from the group consisting of aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, tris(2,3,4,5,6-pentafluorophenyl)borane, hexafluorophosphoric acid, boron trifluoride, boron trifluoride-diethyl ether complex, boron trifluoride acetic acid complex, and boron trifluoride n-propanol complex. The amount of additive selected from the group consisting of Bronsted acids and Lewis acids used is preferably within the range of 0.1 mol% to 10 mol%, more preferably 0.2 mol% to 5 mol%, preferably 0.3 mol% to 2 mol%, in particular 0.4 mol% to 1 mol%, based on the amount of the compound of formula (II). The enantioselective hydrogenation of the compound of formula (II) is carried out in the presence of an iridium chiral catalyst comprising a chiral ligand of formula (Illa), (lllb), (IVa) or (IVb). In a preferred embodiment of the process according to the invention, the substituents of formulas (la), (Ib), (II), (Illa), (lllb), (IVa), (IVb), (IXa) and (IXb) are defined as follows: R1 is Ci-Ce-alkyl or C6-Ci4-aryl-Ci-C4-alkyl, wherein C6-Ci4-aryl in the C6-Ci4-aryl-Ci-C4-alkyl fraction is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. R2 and R3 are equal and are selected from Ci-C4-alkyl, R4 is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl or benzyl, n is 0.1 or 2, Qbhrnn / zznz / E / Yl· Each substituent R5, if present, is independently selected from the group R6 formed by halogen, C1-Ce-alkyl and C1-Ce-haloalkyl, is C1-Ce-alkyl, C1-Ce-haloalkyl, Cs-Cy-cycloalkyl or Ce-Cu-aryl, where the Ce-Cu-aryl is either unsubstituted or substituted by one to five substituents selected from the group formed by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, where the phenyl is again either unsubstituted or substituted by one to five C1-Ce-alkyl substituents. R7 and R8 are independently selected from the group formed by hydrogen, C1-Ce-alkyl, Cs-Cu-aryl, C1-Ce-alkoxy or C1-Ce-haloalkyl, where the Ce-Cu-aryl is not substituted or is substituted by one to five Ci-C4-alkyl substituents, 15 20 25 R9 and R10 are independent of each other selected from the group consisting of Ci-Cealkyl, Ci-Ce-alkoxy, d(Ci-Ce-alkyl)amino, C3-C12-cycloalkyl, Ce-Cuaryl, Ce-Ci4-aryloxy and Ce-Ci4-aryl-Ci-C4-alkyl,where the Ci-Ce-alkyl, Ci-Ce-alkoxy and d(Ci-Ce-alkyl)amino fractions are optionally substituted by 1 to 3 substituents selected independently from the halogen group, Ci-C4-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, where the phenyl can be substituted by one to five substituents selected independently from each other from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and where the Ce-Cu-aryl, Ce-Cu-aryloxy and C3-C12-cycloalkyl, as such or as part of a composite substituent, in each case is either unsubstituted or substituted by one to five substituents selected from the halogen group, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five Ci-Ce-alkyl substituents or 30 R9 and RW m A together with the phosphorus atom to which they are attached, form a phospholane ring,which can be replaced by one or two Ci-Ce-alkyl groups, is 1 or 2, is, Qfrfrenn / zznz / E / Yii Qbhcnn / zznz / e / YiA where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline fraction, R13 is Cs-Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl or Ce-Cu-aryl-C1-C4-alkyl, wherein Ce-Cu-aryl and Ce-Cu-aryl in the C6-C14-aryl-C1-C4-alkyl fraction in each case are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R14 and R15 are, independently of each other, selected from the group consisting of C1Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl and Ce-Cu-aryl-C1-C4-alkyl, wherein the Ce-Cu-aryl and Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl fraction are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-halokoxy and C1-C4-halokoxy, R14 and R15 are, independently of each other, selected from the group consisting of C1Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl and Ce-Cu-aryl-C1-C4-alkyl are substituted or are replaced by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R14 and R15 together with the carbon to which they are attached, form a Cs-Ce-cycloalkyl ring, R16 and R17 are, independently of each other, selected from the group consisting of C1Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl and Ce-Cu-aryl-C1-C4-alkyl, wherein the Ci-Ce-alkyl is optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, C1-C4-alkoxy, Ci-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents selected independently of each other from halogen, Ci-C4-alkyl, phenyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl moiety in each case are either unsubstituted or are substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R16 and R17 together with the phosphorus atom to which they are attached form a phospholane ring, which can be substituted by one or two C1-Ce-alkyl groups, R19 is phenyl, t-butyl, R20 is hydrogen, methyl, 16 R21 is benzyl, methyl, R22 is cyclohexyl, and the additive is selected from the group consisting of hexafluorophosphoric acid, trifluoromethyl sulfonic acid, water, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid, tetrafluoroboric acid diethyl ether complex, Nafion, Amberlyst, 1,1,1,3,3,3-hexafluoro-2(trifluoromethyl)propan-2-ol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6pentafluorophenyl)borane, borane tetrahydrofuran complex, boric acid, aluminum (III) trifluoromethanesulfonate, zinc (II) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes and mixtures thereof, wherein the boron trifluoride complexes are preferably selected from the group consisting of the boron trifluoride-diethyl ether complex, the acetic acid boron trifluoride complex, and the n-propanol boron trifluoride complex. In a more preferred embodiment of carrying out the process according to the invention, the substituents in formulas (1a), (1b), (II), (11a), (IIIb), (IVa), (IVb), (IXa) and (IXb) are defined as follows: Qbhrnn / zznz / E / Yl· R1 is Ci-Ce-alkyl, R2 and R3 R4 are equal and are selected from Ci-C4-alkyl, is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl or benzyl, n is 0, 1 or 2, each substituent R5, if present, is selected independently from the group consisting of halogen, Ci-Ce-alkyl and Ci-Ce-haloalkyl, R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile or phenyl, which is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five Ci-Ce-alkyl substituents, R7 and R8, R9 and RW are independently of each other, hydrogen or Ci-Ce-alkyl, are independently of each other selected from the group consisting of ethyl, isopropyl, sec-butyl, isobutyl, terebutyl, cyclohexyl, cyclopentyl, adamantyl and benzyl, and n is 1 or 2, A is Qbhrnn / 77n7 / E / YIA where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline moiety, R13 is tert-butyl, isopropyl or phenyl, R14 and R15, R16 and R17 are methyl, each being either 2-methylphenyl or 3,5-bismethylphenyl, and the additive is selected from the group consisting of aluminum(III) trifluoromethanesulfonate, scandium(III) trifluoromethanesulfonate, trifluoromethanesulfonate, tris(2,3,4,5,6-pentafluorophenyl)borane, hexafluorophosphoric acid, boron trifluoride and boron trifluoride complexes, where the boron trifluoride complexes are preferably selected from the borodiethyl ether trifluoride complex, the boron trifluoride acetic acid complex and the n-propanol complex of boron trifluoride, R19 is phenyl, R20 is methyl, R21 is benzyl, R22 is cyclohexyl, and the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes, and mixtures thereof, wherein the boron trifluoride complexes are preferably selected from the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex, and the boron trifluoride n-propanol complex. In the most preferred embodiment of the process according to the invention, the substituents of formulas (la), (Ib), (II), (Illa), (lllb) are defined as follows: R1 is Ci-C4-alkyl, R2 and R3 R4 are methyl, is Ci-C4-alkyl, n is 0 or 1 R5 if present, is fluorine, R6phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4methoxyphenyl, 3,5-bis-tere-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4f luorofenyl, 4-trif luoromehtylphenyl, 1-naphthyl, 9-anthracenyl 2,4,6-triisopropylphenyl, 9-f enanthryl or 2,6-diethyl-4-methylf in ilo, R7 is hydrogen, R8 is hydrogen or methyl, R9 and R10 are each the same and are selected from the group consisting of ethyl, isopropyl, tere-butyl, cyclopentyl, adamantyl and cyclohexyl, m is 1. In a preferred embodiment of the process according to the invention, the ligand of formula (Illa) or (lllb) is used. Depending on whether compound (la) or (Ib) is the desired product, the ligand of formula (Illa) or (lllb) is selected. The ligands of the formulas (Illa) and (lllb) are preferred, where the substituents are defined as follows: R6 is Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Cy-cycloalkyl or Ce-Cu-aryl, wherein the C6-Ci4-ahlo is not substituted or is substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and phenyl, wherein again the phenyl is not substituted or is substituted by one to five Ci-Ce-alkyl substituents, R7 and R8 are independent of each other selected from the group consisting of hydrogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C6-Ci4-aryl or Ci-Ce-haloalkyl, wherein the Ce-Cu-aryl is either unsubstituted or substituted by one to five Ci-C4-alkyl substituents, R9 and rioson are independently selected from the group consisting of C1Ce-alkyl, Ci-Ce-alkoxy, di(Ci-Ce-alkyl)amino, Cs-Ci-cycloalkyl, Ce-Cuaryl, Ce-Cu-aryloxy and Ce-Cu-aryl-C1-C4-alkyl, wherein the Ci-Ce-alkyl, Ci-Ce-alkoxy and di(Ci-Ce-alkyl)amino fractions are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, Ci-C4-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents independently selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and where Ce-Cu-aryloxy, C3-C12-cycloalkyl and Ce-Cu-aryl, as such or as part of a compound, in each case is either not substituted or is substituted by Qbhrnn / 77n7 / E / Yl· one to five substituents selected from the group consisting of halogen, CiC4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and phenyl, wherein the phenyl is either unsubstituted or substituted by one to five CiC4-alkyl substituents or R9 and rio together with the phosphorus atom to which they are attached, form a phospholane ring, which can be substituted by one or two Ci-Ce-alkyl groups, ym is 1 or 2. More preferred are the ligands of the formulas (Illa) and (lllb), in which the substituents are defined as follows: R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-enanthryl or phenyl, which is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C4-alkoxy, C4-alkyl, C4-haloalkyl and phenyl, wherein again the phenyl is either unsubstituted or substituted by one to five C4-alkyl substituents. R7 and R8 are independently of each other hydrogen or Oi-Ce-alkyl, R9 and R10 are independently selected from the group consisting of ethyl, isopropyl, sec-butyl, iso-butyl, tere-butyl, cyclohexyl, cyclopentyl, adamantyl and benzyl, and m is 1 or 2. The most preferred are the ligands of the formulas (Illa) and (lllb), in which the substituents are defined as follows: R6 is selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tere-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trif luoromehthylphenyl, 1-naphthyl, 9-anthracenyl 2,4,6-triisopropylphenyl, 9-phenanthryl or 2,6-diethyl-4methylphenyl, R7es hydrogen R8 is hydrogen or methyl, R9 and R10 are equal, being tere-butyl, cyclopentyl or cyclohexyl, and m is 1 In another preferred embodiment of the process according to the invention, the ligand of formula (IVa) or (IVb) is used. Depending on whether compound (a) or (Ib) is the desired product, the ligand of formula (IVa) or (IVb) is selected. The ligands of formulas (IVa) and (IVb) are preferred, in which the substituents are defined as follows: A is Qbhrnn / zznz / E / Yl· Qbhrnn / zznz / E / YiA where the bond identified by * is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline fraction, R13 is Cs-Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl or C6-Cu-aryl-C1-C4-alkyl, wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl fraction in each case are either not substituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R14 and R15 are, independently of each other, selected from the group consisting of C1Ce-alkyl, Ce-Cu-aryl, C3-C12-cycloalkyl and C6-C14-aryl-C1-C4-alkyl, wherein Ce-Cu-aryl and the Ce-Cu-aryl in the C6-C14-aryl-C1-C4-alkyl fraction are either not substituted or are substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R14 and R15 together with the carbon to which they are attached, form a Cs-Cs-cycloalkyl ring, R16 and R17 are, independently of each other, selected from the group consisting of C1Ce-alkyl, C3-C12-cycloalkyl, Ce-Cu-aryl and Ce-Cu-aryl-C1-C4-alkyl, wherein the Ci-Ce-alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents independently selected from each other from halogen, C1-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl moiety in each case are either unsubstituted or are substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, phenyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R16 and R17 together with the phosphorus atom to which they are attached, form a phospholane ring, which can be substituted by one or two Ci-Ce-alkyl groups. More preferred are the ligands of formulas (IVa) and (IVb), in which the substituents are defined as follows: A is where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline fraction, R13 is iso-propyl, sec-butyl, iso-butyl, tere-butyl, phenyl or benzyl, R14 and R15 are, independently of each other, selected from the group consisting of CiCs-alkyl and Ce—aryl—C1—C4—alkyl, wherein the Ce—aryl in the Ce-Cu-aryl-Ci-C4-alkyl fraction is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen and Ci-C4-alkyl, R16 and R17 are, independently of each other, phenyl, 1-naphthyl or 2-naphthyl, which in each case is either unsubstituted or substituted by one to five Ci-C4-alkyl substituents The most preferred are the ligands of formulas (IVa) and (IVb), in which the substituents are defined as follows: A is where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline fraction, R13 is tert-butyl, Ri4yR!5 are methyl, and R16 and R17 are, independently of each other, phenyl, which is substituted by one or two methyl groups, in particular R16 and R17 are each the same and phenyl, which is substituted by one or two methyl groups, or R16 and R17 are each the same and 2-methylphenyl or 3,5-dimethylphenyl. In another preferred embodiment of the process according to the invention, the ligand of formula (IXa) or (IXb) is used. Depending on whether compound (Ia) or (Ib) is the desired product, the ligand of formula (IXa) or (IXb) is selected. The ligands of formulas (IXa) and (IXb) are preferred, in which the substituents are defined as follows: R19 are independently selected from phenyl, benzyl, t-butyl, isopropib, cyclohexyl, R20s are selected independently from hydrogen, methyl, ethyl, isopropyl, R21 are selected independently from hydrogen, benzyl, methyl, ethyl and R22 are independently selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl. More preferred are the ligands of formulas (IXa) and (IXb), in which the substituents are defined as follows: R19 is phenyl, t-butyl, R20 is hydrogen, methyl, R21 is benzyl, methyl, and R22 is cyclohexyl. The most preferred are the ligands of formulas (IXa) and (IXb), in which the substituents are defined as follows: R19phenyl, R20methyl, R21benzyl, and R22cyclohexyl. Preferably, the chiral iridium catalyst is selected from the group consisting of [lrL*(COD)]Y and [lrL*(nbd)]Y, where L* is the chiral ligand of the formulas (Illa), (lllb), (IVa) or (IVb), COD represents 1,5-cyclooctadiene, nbd represents norbornadiene, and And it is a non-coordinating anion selected from the group consisting of [B(R18)4]“, PFe-, SbFe-, CF3SO3', [Al{OC(CF3)3}4]· (formula (Vil)) and Δ- TRISPHAT (formula (VIII)) (V) (VIII) Furthermore, R18 is selected from fluorine and phenyl, which is either unsubstituted or substituted with one to five substituents selected from Ci-C4-alkyl, Ci-C4-haloalkyl, and halogen. The preferred ones are chiral iridium catalysts of the formulas [lrL*(COD)]Y and [lrL*(nbd)]Y, where Y is PF6, [AI{OC(CF3)3}4]· (formula (Vil)) or [B(R13)4]“, where R18 is phenyl, which is either unsubstituted or substituted with one to five substituents selected from fluorine and trifluoromethyl. Even more preferred are chiral iridium catalysts of the general formulas (Va), (Vb), (Via) and (Vlb) R R9' .10 R R” (Goes) [B(r18)4]' Qfrfrenn / zznz / E / YiA [B(r18)4]' where R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile or phenyl, wherein 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile and phenyl are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Cl-C4-alkoxy, Cl-C4-alkyl, Cl-C4-haloalkyl and phenyl, wherein phenyl is again either unsubstituted or substituted by one to five Cl-C4-alkyl substituents, R7 and R8, R9 and RW are independently of each other, hydrogen, Cl-C4-alkyl or Cl-C4-alkoxy are independently of each other selected from the group consisting of ethyl, isopropyl, sec-butyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantil and benzyl, m is 1 or 2, R13 is isopropyl, sec-butyl, isobutyl, tere-butyl, phenyl or benzyl, R14 and R15 are independently selected from each other from the group consisting of Ci-Ce-alkyl and C6-aryl-Ci-C4-alkyl,where the Cs-aryl in the C6-Ci4-aryl-Ci-C4-alkyl fraction is either unsubstituted or substituted by one to five substituents selected from the halogen-Ci-C4-alkyl group, R16 and R17 are independently of each other phenyl, 1-naphthyl or 2-naphthyl, which in each case is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl, and R18 is phenyl, which is either unsubstituted or substituted with one to five substituents selected from fluorine and C1-C4-haloalkyl. Iridium chiral catalysts of the general formulas (Va), (Vb), (Via) and (Vlb) are particularly preferred, where Re is selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tere-butyl-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-f luorophenyl, 4trif luoromehtilphenyl, 1-naphthyl, 9-anthracenyl, 2,4,6-triisopropylphenyl, 9-phenanthril and 216-diethyl-4-methylphenyl, R7 is hydrogen, R8 is hydrogen or methyl R9 and R10 are equal and tere-butyl, adamantil, cyclopentyl or cyclohexyl, m is 1 R13 is tert-butyl, R14 and R15 are methyl, R16 and R17 are independently of each other phenyl, which is substituted by one or two methyl groups, in particular R16 and R17 are the same and 2-methylphenyl or 3,5-dimethylphenyl in the first, and R18 is 3,5-bis(trifluoromethyl)phenyl. The most preferred are chiral iridium catalysts of the general formulas (Va), (Vb), where R6es selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tere-butyl-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-f luorophenyl, 4trif luoromehtilphenyl, 1-naphthyl, 9-anthracenyl, 2,4,6-triisopropylphenyl, 9-phenanthryl and 2,6-diethyl-4-methylphenyl, R7 is hydrogen, R8 is hydrogen or methyl R9 and rioson¡guaieSy tere-butyl, or cyclohexyl, m is 1 The amount of iridium catalyst used is preferably within the range of 0.001 mol% to 5 mol%, more preferably 0.002 mol% to 4 mol%, more preferably 0.005 mol% to 3 mol%, in particular 0.01 mol% to 2.0 mol%, according to the amount of the compound of formula (II). The chiral iridium catalyst can be prepared by methods known in the art from an iridium(I) catalyst precursor, such as [lr(COD)CI]2, the chiral ligand of formula (Illa), (lllb), (IVa) or (IVb) and an alkali salt of the non-coordinating anion (S. Kaiser et al., Angew. Chem. Int. Ed. 2006, 45, 5194-5197; WJ Drury III et al., Angew. Chem. Int. Ed. 2004, 43, 70-74). Preferably, the process according to the invention is carried out in the presence of a chiral iridium catalyst, wherein the chiral iridium catalyst is selected from the group consisting of [lrL*(COD)]Y and [lrL*(nbd)]Y, in which L* is the chiral ligand of the formula (Illa), (lllb), (IVa) or (IVb), COD represents 1,5-cyclooctadiene, Nbd represents norbornadiene, and Y is a non-coordinating anion selected from the group formed by [B(R18)4]“, ρρθ-, SbF6“, CF3SO3', [AI{OC(CF3)3}4]· (formula (Vil)) and Δ- TRISPHAT (formula (VIII)) (VII) (VIII) wherein R18 is selected from fluorine and phenyl, which is either unsubstituted or substituted by one to five substituents selected from Ci-C4-alkyl, Ci-C4-haloalkyl, and halogen, and in the presence of an additive, wherein the additive is selected from the group consisting of hexafluorophosphoric acid, acetic acid, trifluoromethylsulfonic acid, water, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid, tetrafluoroboric acid diethyl ether complex, Nafion, Amberlyst, 1,1,1,3,3,3hexafluoro-2-(trifluoromethyl)propan-2-ol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, borane tetrahydrofuran complex, boric acid, and aluminum trifluoromethanesulfonate (III), zinc trifluoromethanesulfonate (II), scandium trifluoromethanesulfonate (III), aluminum fluoride (III), titanium isopropoxide (IV), trimethylaluminum, boron trifluoride, boron trifluoride complexes and mixtures thereof,where the boron trifluoride complexes are preferably selected from the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex, and the boron trifluoride n-propanol complex. More preferably, the process according to the invention is carried out in the presence of a chiral iridium catalyst, wherein the chiral iridium catalyst is selected from the group consisting of the chiral iridium catalyst of the formulas [lrL*(COD)]Y and [lrL*(nbd)]Y, where L* is the chiral ligand of formula (Illa), (lllb), (IVa) or (IVb), COD represents 1,5-cyclooctadiene, nbd represents norbornadiene, and And it is PF6, [Al{OC(CF3)3}4]· (formula (Vil)) or [B(R18)4], where R18 is phenyl, which is either unsubstituted or substituted by one to five substituents selected from fluorine and trifluoromethyl, and in the presence of an additive, where the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid diethyl ether complex, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, complexes of boron trifluoride and mixtures thereof, wherein the boron trifluoride complexes are preferably selected from the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex and the boron trifluoride n-propanol complex. Even more preferably, the process according to the invention is carried out in the presence of a chiral iridium catalyst, wherein the chiral iridium catalyst is selected from the group consisting of chiral iridium catalysts of formulas (Va), (Vb), (Via) and (Vlb) (Va) (Vb) Qfrfrenn / zznz / E / YiA [B(r18)4]' where R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile, or phenyl, wherein 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile, and phenyl are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, Cl-C4-alkoxy, Cl-C4-alkyl, Cl-C4-haloalkyl, and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five Cl-Cs-alkyl substituents; R7 and R8 are independently of each other hydrogen, Cl-Ce-alkyl, or Cl-Cs-alkoxy; R9 and RW are independently of each other selected from the group consisting of ethyl, isopropyl, sec-butyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, and adamantyl. and benzyl, M is 1 or 2, R13 is isopropyl, sec-butyl, isobutyl, tere-butyl, phenyl or benzyl, R14 and R15 are independent of each other selected from the group formed by Ci-Ce-alkyl and Ce-aryl-Ci-C4-alkyl, where the Ce-aryl in the C6-C14-aryl-C14-alkyl fraction is either unsubstituted or substituted by one to five substituents selected from the halogen-C14-alkyl group, R16 and R17 are independent of each other, phenyl, 1-naphthyl or 2-naphthyl, which in each case is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl, and R18 is phenyl, which is either unsubstituted or substituted by one to five substituents selected from fluorine and Ci-C4-haloalkyl, and in the presence of an additive, wherein the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes, and mixtures thereof, wherein the boron trifluoride complexes are preferably selected from the group consisting of the boron trifluoride-diethyl ether complex, the acetic acid complex of boron trifluoride and the boron trifluoride n-propanol complex. In particular, the process according to the invention is preferably carried out in the presence of a chiral iridium catalyst, wherein the chiral iridium catalyst is selected from the group consisting of chiral iridium catalysts of formulas (Va), (Vb), (Via) and (Vlb), wherein R6 is selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tere-butyl-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 1-naphthyl, 9-anthracenyl, 2,4,6-triisopropylphenyl, 9-phenanthyl, and 2,6-diethyl-4-methylphenyl. R7 is hydrogen, R8 is hydrogen or methyl R9 and R10 are the same and tere-butyl, adamantyl, cyclopentyl or cyclohexyl, m 1 or 2, R13 is tert-butyl, R14 and R15 are methyl, R16 and R17 are independently of each other phenyl, which is substituted by one or two methyl groups, in particular R16 and R17 are the same and 2-methylphenyl or 3,5-dimethylphenyl, and R18 is 3,5-bis(trifluoromethyl)phenyl, and in the presence of an additive, Qbhrnn / zznz / E / Yl· where the additive is selected from the group consisting of aluminum (III) trifluoromethanesulfonate, aluminum (III) trifluoromethanesulfonate, trifluoro(2,3,4,5,6-pentafluorophenyl)borane, hexafluorophosphoric acid, boron trifluoride and boron trifluoride complexes, where the boron trifluoride complexes are preferably selected from the group consisting of the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex and the boron trifluoride n-propanold complex. The process according to the invention comprises the enantioselective hydrogenation of the compound of formula (II). Preferably, hydrogenation is carried out using hydrogen gas at a pressure of 1 to 300 bar, preferably from 3 to 200 bar, and more preferably from 20 to 150 bar. Hydrogenation is preferably carried out at a temperature within the range of 20°C to 130°C, more preferably from 30°C to 100°C. Suitable solvents include halogenated alcohols such as 2,2,2-trifluoroethanol, hexafluoroisopropanol (1,1,1,3,3,3-hexafluoro-2-propanol) and tetrafluoropropanol (2,2,3,3-tetrafluoro-1-propanol), halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-dioxyethane and anisole, and esters such as ethyl acetate, isopropyl acetate and their mixtures. The preferred solvents are selected from the group consisting of 2,2,2-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, 1,4-dioxane, isopropyl acetate, toluene and mixtures thereof. More preferred solvents are selected from the group consisting of 2,2,2-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, and mixtures thereof. 2,2,2-trifluoroethanol and hexafluoroisopropanol are especially preferred. Hexafluoroisopropanol being the most preferred. Qbhrnn / 77n7 / E / Yl· Abbreviations and acronyms: Qfrfrenn / zznz / E / Yii a / a Ac Acetyl c-hexane cyclohexane Cy Cyclohexyl DCM dichloromethane GC-FID Gas Chromatography - Flame Ionization Detector HPLC High-Performance Liquid Chromatography Et Ethyl Me Methyl n-BuL1 n-Butylthiol PTFE Polytetrafluoroethylene RT Room temperature SFC Supercritical Fluid Chromatography THF tetrahydrofuran Tf Trifluoromethylsulfonylmethane TFE 2,2,2-Trifluoroethanol Preparation of iridium catalysts Qfrfrenn / zznz / E / Yii H / Me 1)n-BuLI,THF, -78 °C [lr(COD)2]BARF, THF, 50 °C BARF2) R2PCI, THF, -78 °C to 50 °C The ligand precursors (enantiomerically enriched secondary alcohols) were prepared according to procedures known from the literature as the method disclosed in S. Kaiser et al., Angew. Chem. Int. Ed. 2006, 45, 5194-5197 or in D.H. Woodmansee, Chem. Sci. 2010, 1, 72. The iridium ligands and complexes were prepared by a modified procedure based on the same precedents in the literature: Standard procedures Ligand synthesis procedure (low Ar): A solution of alcohol precursor in THF (0.25 mmol in 5.0 mL THF) was cooled to -78 °C, and n-BuLi (0.1 mL of a 2.5 M n-BuLi solution in hexane; 0.25 mmol; 1 eq) was added dropwise to the continuously stirred solution. After the addition was complete, the solution was allowed to warm to room temperature and stirred at this temperature for an additional 30 minutes. The solution was then cooled to -78 °C again, and R2PCI (0.25 mmol, 1 eq) was added to the continuously stirred solution. The mixture was allowed to warm to room temperature and subsequently heated to 50 °C and held at this temperature overnight. The theoretical yield of the ligand was calculated using 31P-NMR, and the ligand was used for the next step without further purification. Complexation procedure (under Ar): To the crude ligand solution, [lr(COD)2]BARF (BARF = Tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate) was added (as a solid, 1 eq. based on the theoretical yield). The resulting mixture was heated to 50°C and held at this temperature for 3 h. Study (in air): After cooling to room temperature, the reaction solution was rotaryly evaporated over silica, loaded onto a silica column. Side components were eluted using pentane / diethyl ether, and the desired complexes were subsequently eluted with DCM. The solvent was evaporated under reduced pressure. The following catalysts were synthesized and characterized: Qfrfrenn / zznz / E / YiA where m = 1 and R18 = 3,5-bis(trif luoromethyl)phenyl Table 1: Catalizador R6 R7 R8 R9, R10 Va-1 fenilo HH tere-butilo Va-2 fenilo H metilo tere-butilo Vb-3 fenilo HH cyclohexilo Va-4 fenilo H metilo cyclohexilo Vb-5 4-tert-butilf enilo HH cyclohexilo Va-6 4-tert-butilf enilo H metilo cyclohexilo Vb-7 9-antracenilo HH cyclohexilo Va-8 9-antracenilo H metilo cyclohexilo Va-9 2,6—dimetilf enilo H metilo cyclohexilo Va-10 2,4,6-trimetilf enilo H metilo cyclohexilo Va-11 3,5—dimetilf enilo H metilo cyclohexilo Va-12 1-naftilo H metilo cyclohexilo Va-13 4-metoxifenilo H metilo tere-butilo Va-14 4-fluorofenilo H metilo tere-butilo Va-15 4-(trif luorometil)fenilo H metilo tere-butilo Va-16 fenilo H metilo ciclopentilo Vb-17 fenilo HH etilo Va-18 fenilo H metilo isopropilo Va-19 metilo H metilo cyclohexilo Va-20 3,5—bis—tere.—butyl, -4-metoxifenilo H metilo cyclohexilo Va-21 2,4,6-triisopropilf enilo H metilo cyclohexilo Va-22 4—tero-butyl-2,6-dimetilf enilo H metilo ciclohexilo Va-23 fenilo HH adamantilo Va-24 9-fenantrilo H metilo ciclohexilo Catalyst R6 R7 R8 R9, R10 Va-25 2,6-diethyl-4-methylphenyl H methyl cyclohexyl Va-26* 4-tere-butyl-2,6-dimethylphenyl H methyl cyclohexyl The counteranion is PFe instead of BARF Qfrfrenn / zznz / E / Yii Va-2 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (89.5 mg; 53% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.26 (dd, J = 7.9, 1.7 Hz, 2H), 7.81 - 7.36 (m, 16H), 5.75 (dt, J = 8.0, 5.2 Hz, 1H), 5.34 - 5.29 (m, 1H), 4.51 (q, J = 5.3, 3.2 Hz, 1 H), 4.11 (dq, J = 12.5,7.6, 5.9 Hz, 1 H), 3.08 (ddd, J = 16.6,10.3, 3.8 Hz, 1H), 2.99 - 2.70 (m, 2H), 2.61 -2.00 (m, 8H), 1.92-1.79 (m, 1H), 1.69(dd, J= 14.8,8.1 Hz, 1H), 1.51 (s, 9H), 1.29- 1.24 (m, 3H), 1.06 (d, J= 14.4 Hz, 9H). 31P-NMR (122 MHz, CD2C12) δ (ppm) = 142.09. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.85. HR-MS (ESI) m / z calculated for C31 H44NOPIr [M]+ 670.2790 returned 670.2798. Va-4 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (241 mg; 71% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.38 -8.14 (m, 2H), 7.83-7.43 (m, 16H), 5.76 (dt, J = 7.7,4.9 Hz, 1H), 4.81 (t, J = 7.6 Hz, 1H), 4.70-4.46 (m, 1H), 3.56-3.39 (m, 1H), 3.06 (ddd, J = 16.7,10.3, 3.6 Hz, 1H), 2.98-2.73 (m, 2H), 2.71 -2.57(m, 1H), 2.44 (s, 3H), 2.41 -2.02 (m, 6H), 2.00 - 1.75 (m, 7H), 1.72 - 1.54 (m, 4H), 1.46 - 0.94 (m, 13H), 0.72 - 0.50 (m, 1H). 31PRMN (122 MHz, CD2CI2) δ (ppm) = 121.27. 19F-NMR(282 MHz, CD2CI2) δ (ppm) = -62.86. HR-MS (ESI) m / zcalculated for C35H48NOPIr [M]+ 722.3103 returned 722.3116. Vb-5 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (261 mg; 74% based on [lr(COD)2]BARF). H-RMN (300 MHz, CD2CI2): δ (ppm) = 8.25 (d, J = 8.3 Hz, 2H), 7.87 (d, J = 8.1 Hz, 1H), 7.81 -7.64(m, 11H), 7.56 (s, 4H), 5.74(dt, J=8.2,4.6Hz, 1 H), 4.95 - 4.74 (m, 1 H), 4.74-4.51 (m, 1H), 3.60 -3.45 (m, 1 H), 3.23 - 2.91 (m, 2H), 2.90 - 2.70 (m, 1H), 2.67-2.50 (m, 1 H), 2.522.23 (m, 4H), 2.28 - 2.04 (m, 3H), 2.04 - 1.77 (m, 7H), 1.69 - 1.58 (m, 4H), 1.45 - 1.26 (m, 17H), 1.17- 0.95 (m, 4H), 0.68 - 0.42 (m, 1 H). 31P-RMN (122 MHz, CD2CI2) δ (ppm) =121,12. 19F-RMN (282 MHz, CD2C12) δ (ppm) = - 62.85. HR-MS (ESI) m / zcalculado para C38H54NOPIr [M]+ 764.3572 arrojó 764.3586. Va-6 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (286 mg; 64% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CDCh): δ (ppm) = 8.20 (d, J = 8.2 Hz, 2H), 7.77 -7.69 (m, 8H), 7.66 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 4.9 Hz, 5H), 5.77 - 5.67 (m, 1H), 4.78 (d, J = 7.6 Hz, 1H), 4.57 (s, 1H), 3.47 (s, 1H), 3.08 - 2.89 (m, 1H), 2.89 - 2.66 (m, 2H), 2.59 (p, J = 7.4 Hz, 1H), 2.47 - 1.74 (m, 15H), 1.42 (s, 17H), 1.18 - 0.78 (m, 5H), 0.72-0.48 (m, 1H).31P-NMR (122 MHz, CDCh) 121.31. 19F-NMR (282 MHz, CDCI3) δ = - 62.42. HR-MS (ESI): m / z calculated for [C39H56NOP193lr]+: 778.3729 returned 778.3732. Vb-7 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated after two purification times as an orange solid (151 mg; 36% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.84 (s, 1H), 8.38- 8.27 (m, 1H), 8.21 (ddt, J = 8.5, 1.3, 0.7 Hz, 1H), 8.18-8.02 (m, 2H), 7.83-7.72 (m, 10H), 7.72 -7.54 (m, 6H), 7.49 (ddd, J = 8.8, 6.6, 1.4 Hz, 1 H), 7.23 - 6.96 (m, 1H), 5.74- 5.54 (m, 1H), 5.26 - 5.12 (m, 1H), 4.41 -4.18 (m, 1H), 3.53 -3.15 (m, 3H), 2.75-2.61 (m, 2H), 2.59 - 2.32 (m, 2H), 2.18 - 1.91 (m, 6H), 1.92 -1.74 (m, 5H), 1.74-1.56 (m, 2H), 1.48-1.21 (m, 10H), 1.18- 0.99 (m, 1 H), 0.96- 0.59 (m, 2H), 0.39 - 0.15 (m, 1 H), 0.06 —0.11 (m, 1 H). 31P-NMR (122 MHz, CD2CI2) δ (ppm) - 120.30. 19F-NMR (282 MHz, 002012) δ (ppm) = -62.87. HR-MS (ESI) m / zcalculated for C42H50NOPIr [M]+ 808.3259 returned 808.3278. Va-8 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated using DCM (100%) to provide an orange solid (296 mg; 78% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) =8.68 (s, 1H), 8.23- 7.85 (m, 3H), 7.75 - 7.23 (m, 17H), 7.05 (dq, J = 8.8, 1.0 Hz, 1 H), 5.61 - 5.40 (m, 2H), 5.12 - 4.88 (m, 1H), 4.24 - 4.00 (m, 1H), 3.25-2.88 (m, 3H), 2.58-2.46 (m, 2H), 2.44- 2.14 (m, 7H), 2.08-1.61 (m, 11H), 1.61 -1.37 (m, 5H), 1.37- 1.07 (m, 6H), 1.03 - 0.85 (m, 1H), 0.65 - 0.45 (m, 1H), 0.16 (dtd, J= 15.8,10.4, 5.6 Hz, 1H), -0.16 (dt, J= 13.2, 9.1 Hz, 1H). 31P-NMR (122 MHz, CD2CI2) δ = 120.57. 19FRMN (282 MHz, CD2CI2) δ = -62.86. HR-MS (ESI) m / zcalculated for C43H52NOPIr [M]+ 822.3416 returned 822.3416. Va-9 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (298 mg; 82% based on [lr(COD)2]BARF). Qfrfrenn / zznz / E / Yii 1H-RMN (300 MHz, CD2CI2): δ (ppm) = 7.80 - 7.52 (m, 12Η), 7.42 - 7.19 (m, 3Η), 7.12 (d, J = 7.5 Hz, 1H), 5.65 (td, J = 5.6, 2.6 Hz, 1H), 5.48-5.42 (m, 1 H), 4.43 - 4.37 (m, 1H), 3.38-3.30 (m, 1 H), 3.21 - 2.89 (m, 3H), 2.67 (s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, 3H), 2.58-2.45 (m, 2H), 2.42 (s, 3H), 2.67 (s, 3H), 2.58-2.45(m, 2H), 2.42 (s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, 3H), 2.58-2.45(m, 2H),2.42 (s, s, 3H), 2.58-2.45 (m, 2H), 2.42 (s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, S, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, S, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, S, 3H), 2.58-2.45(m. 2H), 2.42 (s, 3H), 2.58 - 2.45 (m, 2H), 2.42 (s, 3H), 2.58-2.45(m, 2H),2.42 (s, 3H), 2.38-2.16 (m, 2H), 2.13 - 2.05 (m, 3H), 2.02 - 1.89 (m, 4H), 1.84 (s, 3H), 1.81 - 1.72 (m, 2H), 1.64- 1.49(m, 3H), 1.39-1.19 (m, 8H), 1.12-0.99 (m, 4H), 0.68 - 0.56 (m, 1H).31PRMN (122 MHz, CD2CI2) δ= 118,80.19F-MRN (282 MHz, CD2CI2) 6 = -62.88. HR-MS (ESI) m / z calculated for C37H52NOPIr [M]+ 750.3416 yielded 750.3420. Va-10 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (148 mg; 40% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 7.91-7.46 (m, 12H), 7.21 (s, 1H), 7.09 (s, 1H), 6.94 (s, 1H), 5.67 - 5.63 (m, 1H), 5.46-5.41 (m, 1H), 4.38 - 4.36 (m, 1 H), 3.36 - 3.32 (m, 1 H), 3.192.85 (m, 3H), 2.64 (s, 3H), 2.53-2.46 (m, 2H), 2.41 (s, 3H), 2.35 (s, 3H), 2.31 -2.18(m,2H), 2.19-1.83 (m, 14H), 1.68-1.54 (m, 6H), 1.38 - 1.20 (m, 5H), 1.14-0.97 (m, 5H), 0.68-0.56 (m, 1H). 31P-NMR (122 MHz, CD2CI2) δ = 118.64. 19F-NMR (282 MHz, CD2CI2) δ = -62.87. HR-MS (ESI) m / zcalculated for C38H54NOPIr [M]+ 764.3572 returned 764.3577. Va-11 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated using DCM (100%) to obtain an orange solid (310 mg; 85% based on [lr(COD)2]BARF). 1H-NMR (300MHz, CD2CI2): δ (ppm) = 7.86 (s, 2H), 7.79-7.47 (m, 13H), 7.36 (s, 1H), 5,795.62 (m, 1 H), 4.78 - 4.74 (m, 1H), 4.57-4.53 (m, 1 H), 3.56 - 3.48 (m, 1 H), 3.13-2.95 (m, 1 H), 2.95 -2.61 (m, 3H), 2.51 (s, 6H), 2.47 - 2.36 (m, 5H), 2.34 - 2.03 (m, 5H), 2.03 - 1.77 (m, 7H), 1.71 - 1.47 (m, 7H), 1.45 - 1.19 (m, 5H), 1.19 - 0.98 (m, 4H), 0.70- 0.62 (m, 1H). 31P-NMR (122 MHz, CD2CI2) δ = 121.65. 19F-NMR (282 MHz, CD2CI2) δ = -62.88. HR-MS (ESI) m / z calculated for C37H52NOPIr [M]+ 750.3416 returned 750.3406. Va-12 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (286 mg; 78% based on [lr(COD)2]BARF). Qfrfrenn / zznz / E / Yii 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.61 -8.48 (m, 1H), 8.28 - 8.15 (m, 1H), 8.11 -7.98 (m, 1 H), 7.98 - 7.81 (m, 1 H), 7.79 - 7.50 (m, 16H), 5.70 (ddd, J = 8.1,4.9, 3.2 Hz, 1H), 5.37 5.25 (m, 1H), 4.79 (d, J= 10.4 Hz, 1H), 3.53-3.41 (m, 1H), 3.13 (ddd, J= 17.2, 9.5,4.9 Hz, 1H), 2.96 (ddd, J= 17.1,9.4, 4.9 Hz, 1H), 2.88 - 2.66 (ΠΊ, 1H), 2.49-2.34 (m, 7H), 2.27-2.14 (m, 1H), 2.09- 1.56 (m, 15H), 1.43 - 1.12 (m, 9H), 1.06- 0.92 (m, 1H), 0.78-0.59 (m, 1H), 0.42-0.25 (m, 1H). 31P-NMR (122 MHz, CD2CI2) δ = 121.69. 19F-NMR (282 MHz, CD2CI2) δ = -62.87. HR-MS (ESI) m / z calculated for C39H50NOPIr [M]+ 722.3259 yielded 722.3262. Va-13 The reaction was carried out according to the standard procedure described above. The theoretical yield of the ligand was 51%. The complex could be isolated as an orange solid (78.0 mg; 39% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CDCh): δ (ppm) = 8.22 (d, J= 8.7 Hz, 2H), 7.80 - 7.63 (m, 8H), 7.63 - 7.43 (m, 5H), 7.16 (d, J = 8.8 Hz, 2H), 5.82- 5.66 (m, 1 H), 5.37-5.22 (m, 1H), 4.56-4.41 (m, 1H), 4.18-4.00(m, 1H), 3.93 (s, 3H), 3.12-2.97 (m, 1H), 2.96 - 2.74 (m, 2H), 2.70 - 2.56 (m, 1H), 2.43 (S,3H), 2.41 -2.03 (m, 4H), 1.96-1.84 (m, 1H), 1.72 (dd, J = 14.6,7.9 Hz, 1H), 1.51 (d, J = 15.0 Hz, 9H), 1.34- 1.23 (m, 3H), 1.05 (d, J= 14.4 Hz, 9H). 31P-NMR (122 MHz, CD2CI2) δ (ppm) = 141.86. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.85. HR-MS (ESI) m / z calculated for C32H46NO2Plr [M]+ 700.2895 returned 700.2899. Va-14 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (245 mg; 70% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CDCh): δ (ppm) = 8.38-8.12 (m, 2H), 7.82-7.63 (m, 8H), 7.51 (s, 5H), 7.44-7.17 (m, 2H), 5.81 - 5.63 (m, 1H), 4.81 -4.67(m, 1H), 4.67 - 4.49 (m, 1H), 3.57-3.35 (m, 1H), 3.05-2.90 (m, 1 H), 2.88 -2.61 (m, 3H), 2.36 (s, 3H), 2.31 -2.04(m, 7H), 2.01 -1.73 (m, 7H), 1.70 - 1.48 (m, 6H), 1.42 - 1.20 (m, 6H), 1.16- 0.97 (m, 4H), 0.63 - 0.40 (m, 1 H). 31P-NMR (122 MHz, CDCh) δ (ppm) = 121.31. 19F-NMR (282 MHz, CDCh) δ (ppm) = -62.43, -106.61. HR-MS (ESI) m / zcalculated for C35H47NOFPIr [M]+ 740.3009 returned 740.3013. Va-15 The reaction was carried out according to the standard procedure described above using 287 mg of [lr(COD)2]BARF (0.225 mmol). The complex could be isolated as an orange solid (180.0 mg; 48% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.46 (d, J = 7.9 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 7.82 -7.38 (m, 13H), 5.83-5.69 (m, 1H), 4.94-4.78 (m, 1H), 4.73-4.54 (m, 1H), 3.65-3.38 (m, 1H), 3.15-2.72 (m, 3H), 2.61 -2.27(m, 7H), 2.25- 2.04 (m, 4H), 2.04 - 1.72 (m, m, 8H), 1.75 - 1.58 (m, 3H), 1.43 - 1.22 (m, 8H), 1.19- 0.93 (m, 1 H), 0.63 - 0.44 (m, 1 H). 31 P-MRI (122 Qfrfrenn / zznz / E / Yii MHz, CD2CI2) δ (ppm) = 121.74. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.88, -63.40. HRMS (ESI) m / zcalculated for C36H47NOF3Plr [M]+ 790.2977 returned 790.2990. Va-16 The reaction was carried out according to the standard procedure described above. The theoretical yield of the ligand was 90%. The complex could be isolated as an orange solid (261 mg; 75% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 8.28 - 8.11 (m, 2H), 7.93 - 7.45 (m, 16H), 5.81 (dt, J= 9.3, 5.0 Hz, 1H), 4.89 (t, J = 6.9 Hz, 1H), 4.72 - 4.51 (m, 1H), 3.86 - 3.66 (m, 1H), 3.18 - 3.04 (m, 1H), 3.04 - 2.57 (m, 4H), 2.49 (s, 3H), 2.46 - 1.61 (m, 18H), 1.56 - 1.36 (m, 5H), 1.36 1.14 (m, 1H), 1.13- 0.93 (m, 1H), 0.77 - 0.66 (m, 1H). 31P-NMR (122 MHz, CD2CI2) δ (ppm) = 129.37. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.88. HR-MS (ESI) m / z calculated for C33H44NOPIr [M]+ 694.2790 returned 694.2789. Vb-17 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (134 mg; 95% purity based on 31PNMR; 39% based on [lr(COD)2]BARF). H-NMR (300 MHz, CDCh): δ (ppm) = 8.00 - 7.92 (m, 2H), 7.81 - 7.76 (m, 1 H), 7.75 - 7.64 (m, 10H), 7.62-7.55 (m, 2H), 7.52 (d, J = 1.9 Hz, 4H), 5.88 (dt, J = 8.3, 4.9 Hz, 1H), 4.52 (dt, J = 8.3, 4.2 Hz, 1H), 4.37 (ddt, J = 7.4, 5.0, 2.5 Hz, 1 H), 3.61 (td, J = 8.0, 3.8 Hz, 1H), 3.17 - 2.64 (m, 4H), 2.34- 1.79 (m, 9H), 1.68- 1.55 (m, 1H), 1.36-0.90 (m, 9H). 31P-NMR (122 MHz, CDCh) δ = 116.36 (major product; 95%), 111.79 (minor species; 5%). 19F-NMR (282 MHz, CDCh) δ = -62.41. HR-MS (ESI) m / zcalculated for C26H34NOPIr [M]+ 600.2006returned 600.2006. Va-18 The reaction was carried out (0.5 mmol scale) according to the standard procedure described above, but after the addition of CIP(iPr)2 was completed, the reaction mixture was stirred at RT for 16 h. The complex could be isolated as an orange solid (605 mg; 85% based on [lr(COD)2]BARF). H-RMN (300 MHz, CDCh): δ (ppm) = 8.17 (dd, J= 7.1, 1.8 Hz, 2H), 7.78 - 7.40 (m, 16H), 5.74 (dt, J= 9.0, 4.7 Hz, 1H), 4.83 (t, J = 6.9 Hz, 1H), 4.61 (dt, J = 8.7, 4.1 Hz, 1H), 3.62 -3.53 (m, 1H), 3.11 -2.94(m, 1 H), 2.91 -2.67(m, 2H), 2.67 - 2.44 (m, 2H), 2.39 (s, 3H), 2.36 - 1.93 (m, 6H), 1.85 (dd, J = 14.5, 7.3 Hz, 1H), 1.46 (dd, J = 15.2, 7.1 Hz, 3H), 1.39 - 1.31 (m, 1H), 1.23 (dd, J= 13.3,6.9 Hz, 4H), 1.08 (dd, J = 19.4, 7.1 Hz, 3H), 0.52 (dd, J= 15.5, 7.1 Hz, 3H). 31PRMN (122 MHz, CDCh) δ (ppm) = 129,53. 19F-RMN (282 MHz, CDCh) δ (ppm) = -62,42. HR-MS (ESI) m / zcalculado para C29H40NOPIr [M]+ 642.2477 arrojó 642.2480. Va-19 Qfrfrenn / zznz / E / Yii The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (249 mg; 73% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 7.81 -7.61 (m, 9H), 7.56 (d, J = 2.0 Hz, 4H), 7.34 (d, J = 8.0 Hz, 1 H), 5.76 (dt, J = 8.7, 4.5 Hz, 1H), 5.05 - 4.84 (m, 2H), 3.74 - 3.57 (m, 1 H), 3.56 3.36 (m, 1 H), 3.07 (s, 3H), 3.01 - 1.49 (m, 23H), 1.42 - 1.01 (m, 9H), 0.85 - 0.70 (m, 1 H), 0.51 -0.25(m, 1H).31P-NMR (122 MHz, CD2CI2) δ (ppm) = 126.20. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.88. HR-MS (ESI) m / z calculated for C29H44NOPIr [M]+ 644.2766 returned 644.2762. Va-20 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (164 mg; 42% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 7.86-7.62 (m, 10H), 7.56 (s, 4H), 7.38 (s, 1H), 5.72 (dt, J = 8.1,5.2 Hz, 1 H), 4.85 - 4.63 (m, 2H), 3.80 (s, 3H), 3.49 -3.30 (m, 1H), 3.18 - 2.60 (m, 4H), 2.54 - 2.23 (m, 6H), 2.23 - 1.57 (m, 16H), 1.53 - 1.49 (m, 20H), 1.46 - 0.93 (m, 10H). 31P-NMR (122 MHz, CD2CI2) δ (ppm) = 123.26. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = 62.87. HR-MS (ESI) m / z calculated for C44H66NO2Plr [M]+ 864.4460 returned 864.4448. Va-21 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (51 mg; 14% based on [lr(COD)2]BARF). 1H-NMR (400 MHz, CD2CI2): δ (ppm) = 7.80 - 7.64 (m, 8H), 7.56 (s, 4H), 7.23 (s, 2H), 7.04 (s, 1H), 5.65 (dt, J = 5.9, 3.7 Hz, 1H), 5.45 - 5.35 (m, 1H), 4.04 (ddd, J = 8.2, 5.4, 3.6 Hz, 1 H), 3.34 (dd, J = 11.2, 6.4 Hz, 1 H), 3.19 - 3.08 (m, 3H), 3.06 - 2.89 (m, 2H), 2.56 - 2.44 (m, 2H), 2.41 (s, 3H), 2.33 - 1.84 (m, 9H), 1.84-1.43 (m, 15H), 1.35- 1.24 (m, 12H), 1.23 - 1.14 (m, 5H), 1.09 (dd, J = 10.0, 6.8 Hz, 6H), 0.95 (d, J = 6.6 Hz, 3H), 0.60 - 0.46 (m, 1H). 31P-NMR (162 MHz, CD2CI2) δ (ppm) = 119.43. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.86. HR-MS (ESI) m / z calculated for C44H66NOPIr [M]+ 848.4511 found 848.4512. Va-22 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (274 mg; 73% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 7.79 - 7.66 (m, 8H), 7.56 (s, 4H), 7.29 (s, 1 H), 7.23 (s, 1H), 7.13 (s, 1 H), 5.65 (td, J = 5.9, 2.2 Hz, 1 H), 5.46 -5.40 (m, 1 H), 4.42 -4.36 (m, 1 H), 3.383.30 (m, 1 H), 3.19 - 2.86 (m, 3H), 2.65 (s, 3H), 2.59 - 2.44 (m, 2H), 2.42 (s, 3H), 2.38 - 1.54 (m, 20H), 1.46-0.98 (m, 21H), 0.70 - 0.58 (m, 1H).31P-NMR (122 MHz, CD2CI2) δ (ppm) = 118.67. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.86. HR-MS (ESI) m / z calculated for C41 H60NOPIr [M]+ 806.4042 returned 806.4053. Qfrfrenn / zznz / E / Yii Va-23 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (15.6 mg; 20% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2) δ = 8.43 - 8.36 (m, 2H), 7.92-7.85 (m, 1H), 7.81 - 7.69 (m, 12H), 7.68 - 7.53 (m, 4H), 5.73 - 5.65 (m, 1H), 5.50 - 5.43 (m, 1H), 4.58 - 4.43 (m, 2H), 3.25 - 3.12 (m, 1H), 3.08 - 2.94 (m, 1H), 2.92 - 2.77 (m, 1H), 2.72 - 1.45 (m, 40H). 19F-NMR (282 MHz, CDCI3) δ = -62.42. 31P-NMR (122 MHz, CD2CI2) δ = 134.32. HR-MS (TOF) m / zcalculated for C42H54NOPIr [M]+ 812.3572 returned 812.3578. Va-24 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (274 mg; 72% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2) δ = 8.99-8.77 (m, 3H), 8.04-7.63 (m, 15H), 7.56 (s,4H), 5.725.63 (m, 1H), 4.88-4.83 (m, 1H), 4.74-4.68 (m, 1 H), 3.49 - 3.40 (m, 1 H), 3.27-3.07 (m, 1 H), 3.08-2.91 (m, 1H), 2.86-2.74(m, 1H), 2.61 -2.36(m,6H), 2.19(ddd, J= 15.6, 13.8,8.1 Hz, 1H), 2.11-1.11 (m, 25H), 0.99 - 0.66 (m, 3H). 31P-NMR(122 MHz, CD2CI2) δ = 121.93. 19FRMN (282 MHz, CD2CI2) δ = -62.86. HR-MS (ESI) m / z calculated for C43H52NOPIr [M]+822.3410 returned 822.3436. Va-25 The reaction was carried out according to the standard procedure described above. The complex could be isolated as an orange solid (282 mg; 76% based on [lr(COD)2]BARF). 1H-NMR (300 MHz, CD2CI2): δ (ppm) = 7.73 (s, 8H), 7.56 (s, 4H), 7.23 (s, 1H), 7.14 (s, 1 H), 7.00 (s, 1 H), 5.62 (dd, J = 8.0, 5.6 Hz, 1 H), 5.46-5.39 (m, 1H), 4.32 (dd, J = 7.4, 3.4 Hz, 1 H), 3.36-3.27 (m, 1H), 3.19-3.06 (m, 2H), 3.01 -2.91 (m, 2H), 2.80 (dq, J = 14.9, 7.4 Hz, 1H), 2,592.43 (m, 2H), 2.43-2.15 (m, 7H), 2.15-0.83(m, 36H), 0.66-0.48 (m, 1H).31P-NMR (122MHz, CD2CI2) δ (ppm) = 119.00. 19F-NMR (282 MHz, CD2CI2) δ (ppm) = -62.87. HR-MS (ESI) m / z calculated for C40H58NOPIr [M]+792.3880 returned 792.3903. Va-26 A solution of the respective alcohol precursor in THF (0.25 mmol in 5.0 mL of THF) was cooled to -78°C, and n-BuLi (0.1 mL of a 2.5 M n-BuLi solution in hexane; 0.25 mmol; 1 eq) was added dropwise to the continuously stirred solution. After the addition was complete, the solution was allowed to warm to room temperature and stirred at this temperature for an additional 30 minutes. The solution was then cooled again to -78°C, and CysPCi (0.25 mmol, 1 eq) was added to the continuously stirred solution. The mixture was allowed to warm to room temperature and subsequently heated to 50°C and held at this temperature overnight. After the reaction was cooled to RT, THF was removed and dried under vacuum, [lr(cod)CI]2 (0.125 mmol) and DCM (5.0 mL) were added to the tube, and it was shaken at 50°C for 2 h. Then KPFe (0.25 mmol) was added to the reaction mixture and it was shaken at RT overnight.The reaction solution is rotaryly evaporated over silica, loaded onto a silica column prepared with DCM chromatography with EtOAc / DCM: 1 / 10 to obtain the orange solid after two column chromatography runs (130 mg, 55%). 1H-NMR (300 MHz, CD2CI2) δ = 7.37 - 7.02 (m, 3H), 5.74 - 5.56 (m, 1H), 5.52 - 5.46 (m, 1 H), 4.47 - 4.30 (m, 1 H), 3.45 - 3.21 (m, 1H), 3.19 - 2.92 (m, 3H), 2.66 (s, 3H), 2.63 - 2.48 (m, 2H), 2.44 (s, 3H), 2.40 - 2.19 (m, 2H), 2.16 - 1.70 (m, 15H), 1.68 - 1.46 (m, 6H), 1.41 - 1.28 (m, 13H), 1.18 - 0.95 (m, 5H), 0.71 - 0.58 (m, 1H). 31P-NMR (122 MHz, CD2CI2) δ = 118.42, 127.01, -132.85, -138.70, -144.55, -150.39, -156.24, -162.09. 19F-NMR (376 MHz, CD2CI2) δ = -72.64, -74.52. HR-MS (ESI) m / z calculated for ΟαιΗθοΝΟΡΙγ [M]+806.4036 returned 806.4061. Examples The reactions were carried out in metal autoclaves. The reaction mixtures were analyzed without studies by HPLC chromatography (CHIralpak IC column, 95 / 5 heptane / ethanol, 1 mL / min) or SFC (OZ-H column, 2.5% MeOH in supercritical CO2, 3 mL / min). The Ir Va-25 complex (given catalytic load) and 0.64 g 1-(2,2,4-trimethyl-1-quinol)ethanone (3 mmol, purified with heptane: water wash + crystallization) were placed in an 8 mL autoclave vial containing a PTFE-coated stirring rod. The autoclave vial was sealed with a septum screw cap and rinsed with argon (10 min). Hexafluoroisopropanol (HFIP, 4 mL) and the additive (administered load) were added through the septum into the vial. The vial was placed in an argon-containing autoclave, and the autoclave was rinsed with argon (10 min). The autoclave was pressurized with hydrogen gas (10 bar) and subsequently depressurized to atmospheric pressure three times. After this, the autoclave was pressurized to a hydrogen pressure of 60 bar and placed in a suitable alumina block. After heating the reaction to 85°C, it was maintained at this temperature for the specified time.After cooling to room temperature and depressurizing, the vial was removed from the autoclave and the results of the reactions were determined by GC-FID analysis (diluted with EtOH) and the enantiomeric excess by HPLC analysis. Typical values ​​are indicated. Qfrfrenn / zznz / E / Yii Qfrfrenn / zznz / E / YiAi Table 2: Example Additive (mol%) Reaction time (h) catalyst loading (mol%) GC conversion (%a / a) Enantiomeric excess (%ee) 1 — 16 0.02 95.3 nd 2 — 21 0.02 95.5 95.5 nd 3 — 3 0.02 0.02 5.02 0.46 nd 3 — 3 97.6 nd 5 Pentafluorophenol(l) 16 0.02 97.2 nd 6 1,2,2,6,6-pentamethylpiperidine (1) 16 0.02 67.1 nd 7 Alcohol and anatofluoro-tercbutyl (1) 16 0.0 9 6 6 3 8 Alcohol nonafluoro-tert-butyl (5) 16 0.03 97.5 nd 9 3,5-bis- triph luorophenol (1) 16 0.02 95.7 nd 10 AcOH (1) 16 0.02 96 nd 11 AcOH (5) 3 0.06 nd 12 AcOH (5) 3 0.02 63.7 nd 13 AcOH (20) 3 0.02 54.2 nd 14 HPF6 (1) 3 0.02 >99 nd 15 HBF4OEt2 (1) 16 0.02 90.5 nd 16 TfOH(1) 16.0 6.9 nd 67 Sc(OTf)3(1) 3 0.02 >99 99 18 BF3OEt2 (1) 3 0.02 98.9 98 19 BH3* THF(1) 3 0.02 69.8 nd 20 BF3* AcOH (1) 3 0.02 nd BF3* 2-1-1 3 0.02 >99 nd 22 AI(OTf)3(1) 3 0.02 >99 nd 23 AIF3 (1) 3 0.02 65.9 nd 24 AIMes (1) 3 0.02 91.1 nd 25 Ti(O'Pr)4(1) 20.7 nd 2060 BPh3(1) 3 0.02 85.4 nd Example Additive (mol%) Reaction time (h) Catalytic loading (mol%) GC conversion (%a / a) Enantiomeric excess (%ee) 27 B(C6F5)3 (1) 3 0.02 >99 97.6 28 B(C6F5)3 (0.5) 3 0.02 97.3 nd 29 B(C6F5)3 (0.1) 3 0.02 63.3 nd 30 B(OH)3(1) 3 0.02 72.7 nd Examples 31-36: The Ir Va-25 complex (given catalytic charge) and 1-(2,2,4-trimethyl-1-quinolyl)ethanone (given amount; purified with heptane: water wash + crystallization) were placed in a 25 mL autoclave. The autoclave was rinsed with argon (10 min). Hexafluoroisopropanol (1.33 mL per mmol of 1-(2,2,4-trimethyl-1-quinol)ethanone) and additive (given charge) were added to the autoclave. The autoclave was pressurized with hydrogen gas (10 bar) and subsequently depressurized to atmospheric pressure three times. After this, the autoclave was pressurized to a hydrogen pressure of 60 bar and placed in a suitable alumina block. After heating to 85°C, the reaction was maintained at this temperature for the given time. After cooling to room temperature and depressurization, the outcome of the reactions was determined by GC-FID analysis (diluted with EtOH) and the enantiomeric excess by HPLC analysis. Table 3: Example Additive (mol%) Scale (amount of compound (II)) Reaction time (h) Catalytic loading (mol%) GC Conversion (%a / a) Enantiomeric excess (%ee) 31 — 9 mmol 6 0.01 50.8 nd 32 B(C6F5)3 (0.5) 9 mmol 20 0.01 85.2 nd 33 BFsOEts (1) 10 mmol 16 0.01 99.2 nd 34 Al(OTf)3(1) 10 mmol 16 0.01 >99 nd 35 HPF6 (1) 9 mmol 16 0.01 97.3 nd 36 BF3* AcOH (1) 9 mmol 16 0.01 98.1 nd Examples 37-54: The Ir complex (identifier and given catalytic charge) and 0.64 g of 1-(2,2,4-trimethyl-1-quinol)ethanone (3 mmol, purified with heptane: water wash + crystallization) were placed in an 8 mL autoclave vial containing a PTFE-coated stirring rod. The autoclave vial was sealed with a septum screw cap and rinsed with argon (10 min). Hexafluoroisopropanol (HFIP, 4 mL) and BF3*OEt2 (1 mol% with respect to 1-(2,2,4-trimethyl-1-quinol)ethanone) were added through the septum into the vial. The vial was placed in an argon-containing autoclave, and the autoclave was rinsed with argon (10 min). The autoclave was pressurized with hydrogen gas (10 bar) and subsequently depressurized to atmospheric pressure three times. After this, the autoclave was pressurized to a hydrogen pressure of 60 bar and placed in a suitable alumina block. After heating to 85°C, the reaction was maintained at this temperature for the specified time.After cooling to room temperature and depressurizing, the vial was removed from the autoclave and the reaction results were determined by GC-FID analysis (diluted with EtOH) and the enantiomeric excess by HPLC analysis. Typical values ​​are indicated. Table 4: Example Catalyst Additive (mol%) Reaction time (h) Catalytic loading (mol%) GC conversion (%a / a) Enantiomeric excess (%ee) 37 Va-26 — 3 0.02 78.8 98.8 38 Va-26 BF3OEt2 (1) 3 0.02 94.2 99 39 Va-22 — 3 0.02 85.2 98.5 40 Va-22 BF3*OEt2 (1) 3 0.02 >99 98.7 41 Va-15 — 16 0.025 9.4 nd 42 Va-15 — 16 0.05 34.6 83.2 43 Va-15 BF3*OEt2 (1) 16 0.025 82 89.2 44 Vb-7 — 16.5 0.025 79.5 97.5 45 Vb-7 BF3*OEt2 (1) 16 0.025 >99 98.3 46 Va-9 — 16.5 0.025 81.7 97.9 47 Va-9 BF3OEt2 (1) 16 0.025 >99 98.8 48 Va-11 — 16.5 0.025 42.2 94.5 49 Va-11 BF3*OEt2 (1) 16 0.025 82.4 97.7 50 Va-21 — 16 0.025 74 98 51 Va-21 BF3*OEt2 (1) 16 0.025 >99 99.4 52 Vb-5 — 16 0.025 64.4 nd 53 Vb-5 — 16 0.05 98.4 96.8 54 Vb-5 BF3OB2 (1) 16 0.025 >99 97.7 Qbhrnn / zznz / E / Yl· Examples 55-58: The Ir Va-25 complex (0.02 mol%, 0.6 pmol) and 0.64 g 1-(2,2,4-trimethyl-1-quinolyl)ethanolone (3 mmol, purified with heptane: water wash + crystallization) were placed in an 8 mL autoclave vial containing a PTFE-coated stirring rod. The autoclave vial was sealed with a septum screw cap and rinsed with argon (10 min). 2,2,2-Trifluoroethanol (TFE, 4 mL) and BF3*OEt2 (given charge) were added through the septum to the vial. The vial was placed in an argon-containing autoclave, and the autoclave was rinsed with argon (10 min). The autoclave was pressurized with hydrogen gas (10 bar) and subsequently depressurized to atmospheric pressure three times. After this, the autoclave was pressurized to a hydrogen pressure of 60 bar and placed in a suitable alumina block. After heating to 85°C, the reaction was maintained at this temperature for 3 h.After cooling to room temperature and depressurizing, the vial was removed from the autoclave and the results of the reactions were determined by GC-FID analysis (diluted with EtOH) and the enantiomeric excess by HPLC analysis. Typical values ​​are indicated. Table 5: Example BFs*OEÍ2 (mol%) GC Conversion (%a / a) 55 — <1 56 1 86 57 3 88 58 5 82 Examples 59 v60: The iridium catalyst (1) of DE112015001290 T5 is an example of the catalytic structures of formula (IXb). Also using this catalyst, the presence of BFsOEtz has a strong influence on the conversion and a slightly positive influence on ee (General conditions: 0.2 mol% catalyst (I) of DE112015001290 T5, 40°C, 30 bar H2, starting material concentration 0.1 M in trifluoroethanol). Qfrfrenn / zznz / E / YiA IR Catalyst (1) of DE112015001290 T5 Table 5: Example Additive Reaction Time Conv. [%] ee [%] Example 59-1 — 4 am 33 79 Example 59-2 — 4 pm 35 79 Example 60-1 1 mol% BF3OEt2 4 am 75 83 Example 60-2 1 mol% BF3OEt2 4 pm 80 82 NOVELTY OF THE INVENTION Having described the present invention as above, it is considered novel and, therefore, the contents contained in the following are claimed as property: Qfrfrenn / zznz / E / Yii

Claims

1. A process for preparing a compound of formula (a) or (b), wherein R1 is selected from the group consisting of Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Cs-Ce-cycloalkyl, Ce-Cu-aryl, or CeCu-aryl-Ci-C4-alkyl, wherein the Ci-Ce-alkyl, Cs-Ce-cycloalkyl, and Ci-Ce-alkoxy moiety in the Ci-Ce-alkoxy-Ci-Ce-alkyl group are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, Ci-C4-alkoxy-, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, and phenyl, wherein the phenyl can be substituted by one to five substituents independently selected from each other from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-CiC4-alkyl fraction in each case are either not substituted or are substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,R2 and R3 are the same and are selected from the group formed by hydrogen, Ci-Cealkyl, Ci-Ce-haloalkyl - and Ci-Ce-alkoxy- C1-Ce-alkyl, or R2 and R3 together with the carbon to which they are attached, form a CsCe-cycloalkyl ring, R4 is hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylamino, C2-Ce-alkenyl, C2-Ce-alkylene, Cs-Cecycloalkyl, Cs-Ce-cycloalkyl- Ci-C4-alkyl, C2-Ce-alkenyloxy-, 948 fluororenylmethyleneoxy, Ce-Cu-aryl, Ce-C14-aryloxy, Ce—C14—aryl— CeCu-alkyloxy or Ce-Cu-aryl-Ce-Cu-alkyl, wherein the Ce-Cu-aryl as such or as part of a compound substituent is unsubstituted or is substituted by one to five substituents selected from the group consisting of halogen, C4-alkyl, C1-C4-haloalkyl, C4-alkoxy and C4-haloalkoxy, n being 0, 1, 2, 3 or 4, each substituent R5, if present, is independently selected from the group consisting of halogen, C4-alkyl, C4-haloalkyl, C4-alkoxy, hydroxyl,amino and -C(=O)-Ci-Ce-alkyl, comprising the enantioselective hydrogenation of a compound of formula (II) Qbhrnn / zznz / E / Yl· where the substituents R1, R2, R3, R4, R5 and the integer n are each as defined for the compound of formula (a) or (Ib), in the presence of a chiral iridium catalyst, characterized in that the chiral iridium catalyst comprises a chiral ligand of formula (I1a), (I1b), (IVa), (IVb), (IXa) or (IXb), (a) (I1b) R6, R7 and R8 are independently selected from each other from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, C2-C6-alkenyl, C2-C6-alkylyne, C3-C7-cycloalkyl, C307-cycloalkyl-Ci-C4-alkyl, Cs-Cu-aryl and C6-Ci4-aryl-Ci-C4alkyl, where the Ci—Ce—alkyl, C2-C6-alkenyl, C2-C6-alkynyl,C3-C7cycloalkyl and the C3-C7-cycloalkyl in the Cs-Cy-cycloalkyl-Ci-C4-alkyl fraction are optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-alkoxy, and Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-CiC4-alkyl fraction are optionally substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five Ci-Ce-alkyl substituents, R9 and R10 being independently the one selected from the group consisting of Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkyline, Ci-Ce-alkoxy, di(Ci-C6-alkyl)amino, C3-Ci2-cycloalkyl, C3-Ci2-cycloalkyl-C1C4-alkyl, Ce-Cu-aryl, C6-Ci4-aryloxy and Ce-Cu-aryl-Ci-C4-alkyl, where Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,Ci-Ce-alkoxy and di(Ci-C6-alkyl)amino are optionally substituted by 1 to 3 substituents selected independently from the group consisting of halogen, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl can be substituted by one to five substituents selected independently from each other from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, and wherein the C6-Ci4-aryl, C6-Ci4-aryloxy and C3-Ci2-cycloalkyl, in each case either as such or as part of a compound substituent, are optionally substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, CiC4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and phenyl, wherein the phenyl is not substituted or is substituted by one to five CiC4-alkyl or R9 substituents and together with the phosphorus atom to which they are attached, they form a phospholane ring, which may be substituted by one or two Ci-C4-alkyl groups,or R9 and R10 together form x jSL|HRl2)qxo, Λ yy XX^(Rl2)q G1 = po G2 = p where the bonds identified by xey are directly attached to the phosphorus atom, pyq are independently selected from each other from 0, 1 and 2, R11 and R12 are independently selected from Ci-Cealkyl and phenyl, which can be substituted by one to five substituents selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-alkoxy and phenyl, which can be substituted by one or two Ci-C4-alkyl substituents, m is 1 or 2, A is where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline moiety, R13 is Ci-Ce-alkyl, Ci-Ce-haloalkyl, C3-C12-cycloalkyl, C3-C12cycloalkyl— C1-C4-alkyl, C1-C4-alkyl- Cs-Cy-cycloalkyl, Ce-Quaryl or Ce-Quaryl- Ci-C4-alkyl,where the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1C4-alkyl fraction in each case are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, R14 and R15 being independently selected from the group consisting of hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C3-C12cycloalkyl, Cs-Cy-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-Cs-Cycycloalkyl, Ce-Cu-aryl, and Ce-Cu-aryl-C1C4-alkyl, where the Ce-Cu-aryl and the Ce-Cu-aryl in the Ce-Cu-aryl-C1C4-alkyl fraction in each in case they are not substituted or are substituted by one to five substituents selected from the group formed by halogen, C1C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or R14 and R15 together with the carbon to which they are attached, form a Cs-Cecycloalkyl ring, R16 and R17 are independent of each other selected from the group formed by Ci-Ce-alkyl,C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Cealkoxy, di(Ci-Ce-alkyl)amino, C3-Ci2-cycloalkyl, C3-C12-cycloalkyl-C1-C4-alkyl, Ce-Cu-aryl, Ce-Cu-aryloxy and Ce-Cu-C1C4-alkyl, wherein the Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Cealkoxy, Ci-Ce-cycloalkyl and di(Ci-Ce-alkyl)amino groups are optionally substituted by 1 to 3 substituents selected independently from the halogen group, Ci-C4-alkoxy, C1C4-haloalkyl, Ci-C4-haloalkoxy and phenyl, wherein the phenyl group can be substituted by one to five substituents independently selected from among halogen, C1-C4-alkyl, phenyl, C6-C4-alkoxy, C6-C4-haloalkyl, and C3-C2-haloalkoxy, and wherein the Ce-Cu-aryl, the Ce-Cu-aryl in the Ce-Cu-aryl-C1-C4-alkyl, the C6-C14-aryloxy, and the C3-C12-cycloalkyl, in each case either as such or as part of a compound substituent, are optionally substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, phenyl,Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or R16 and R17 together with the phosphorus atom to which they are attached, form a phospholane ring, which may be substituted by one or two Ci-Ce-alkyl groups, or R16 and R17 together form Qbhrnn / 77n7 / E / Yl· where the bonds identified by x and y are both directly attached to the phosphorus atom, p and q are independently selected from each other from 0, 1 and 2, and R11 and R12 are independently selected from Ci-Ce-alkyl and phenyl, which may be substituted by one to five substituents selected from the group formed by halogen, Ci-C4-alkyl, Ci-C4-alkoxy and phenyl, which may be substituted by one or two Ci-C4-alkyl substituents, R19 is independently selected from phenyl, benzyl, t-butyl, isopropyl, cyclohexyl, R20 are independently selected from hydrogen, methyl, ethyl, isopropyl, R21 are independently selected from hydrogen, benzyl, methyl, ethyl,R22 are independently selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, and in the presence of an additive, wherein the additive is selected from the group consisting of Bronsted acids, Lewis acids and mixtures thereof.

2. The process according to claim 1, wherein the additive is selected from the group consisting of hexafluorophosphoric acid, acetic acid, trifluoromethylsulfonic acid, water, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid, tetrafluoroboric acid diethyl ether complex, Nafion, Amberlyst, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, borane tetrahydrofuran complex, boric acid, aluminum(III) trifluoromethanesulfonate, zinc(II) trifluoromethanesulfonate, scandium(III) trifluoromethanesulfonate, aluminum(III) fluoride, titanium isopropoxide (IV), trimethyl aluminum, boron trifluoride, boron trifluoride complexes and mixtures thereof.

3. The process according to claim 1 or 2, wherein the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, trifluorophenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes, and mixtures thereof.

4. The process according to claim 1, wherein R1 is Ci-Ce-alkyl, R2 and R3 are equal and selected from Ci-C4-alkyl, R4 is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl or benzyl, n is 0, 1 or 2, each R5 substituent, if present, is independently selected from the halogen, Ci-Ce-alkyl and Ci-Ce-haloalkyl group, R6 is selected from the 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenantrile or phenyl group, which is either unsubstituted or substituted by one to five substituents selected from the halogen, Ci-C4 alkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five substituents; Ci-Ce-alkyl, R7 and R8 are independently of each other hydrogen or Ci-Ce-alkyl, R9 and R10 are independently of each other selected from the group consisting of ethyl, isopropyl, sec-butyl, isobutyl, tert-butyl, cyclohexyl,cyclopentyl, adamantyl and benzyl, ym is 1 or 2, A is Qbhrnn / zznz / E / Yl· where the bond identified by is directly attached to the phosphorus atom and where the bond identified by # is directly attached to the oxazoline moiety, R13 is tert-butyl, isopropyl or phenyl, R14 and R15 are methyl, R16 and R17 are equal and 2-methylphenyl or 3,5-bismethylphenyl, R19 is phenyl, t-butyl, R20 is hydrogen, methyl, R21 is benzyl, methyl, R22 is cyclohexyl, and where the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, triphenylborane, tris[3,5bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethylaluminum, boron trifluoride, boron trifluoride complexes and mixtures thereof.

5. The process according to claim 1, wherein R1 is Ci-C4-alkyl, R2 and R3 are methyl, R4 is Ci-C4-alkyl, n is 0 or 1, R5 if present, is fluorine, and is characterized in that the chiral iridium catalyst comprises a chiral ligand of the formula (11a) or (11b), Qbhrnn / 77n7 / E / Yl· (11a) wherein R6 is phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tere-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 1-naphthyl, 9-anthracenyl 2,4,6-triisopropylphenyl, 9-phenanthryl or 2,6-diethyl-4-methylphenyl, R7 is hydrogen, R8 is hydrogen or methyl, R9 and R10 are equal and selected from the group consisting of ethyl, isopropyl, tert-butyl, cyclopentyl, adamantyl and cyclohexyl, m is 1, R19 is phenyl, R20 is methyl, R21 is benzyl, R22 is cyclohexyl, and wherein the additive is selected from the group consisting of aluminum(III) trifluoromethanesulfonate, scandium(III) trifluoromethanesulfonate, tris(2,3,4,5,6-pentafluorophenyl)borane, hexafluorophosphoric acid, boron trifluoride, the boron trifluoride-diethyl ether complex, the boron trifluoride acetic acid complex, and the boron trifluoride n-propanol complex.

6. The process according to any one of claims 1 to 5, wherein R1 is Ci-Ce-alkyl or C6-Ci4-aryl-Ci-C4-alkyl, wherein Ce-Cu-aryl in the Ce-Cu-aryl-Ci-C4-alkyl moiety is unsubstituted or is substituted by one to five substituents selected from the halogen group, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, R2 and R3 are equal and are selected from Ci-C4-alkyl, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl or benzyl, n is 0, 1 or 2, each R5 substituent, if present, is selected independently from the halogen group, Ci-Ce-alkyl and Ci-Ce-haloalkyl.

7. The process according to any one of claims 1 to 6, wherein R1 is methyl, ethyl or n-propyl, R2 and R3 are methyl, R4 is Ci-C4-alkyl, n is 0, 1 or 2, each substituent R5, if present, is selected independently of the halogen and Ci-Ce-alkyl group.

8. The process according to any of claims 1 to 7, wherein hydrogenation is carried out using hydrogen gas at a pressure of 1 to 300 bar.

9. The process according to any one of claims 1 to 8, wherein the amount of chiral iridium catalyst used is within the range of 0.001 mol% to 5 mol%, based on the amount of the compound of formula (II).

10. The process according to any of claims 1 to 9, wherein the hydrogenation is carried out at a temperature within the range of 20°C to 130°C.

11. The process according to any of claims 1 to 10, wherein the hydrogenation is carried out in the presence of a solvent selected from the group consisting of 2,2,2,-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol, 1,2-dichloroethane, tetrafluoropropanol and mixtures thereof.

12. The process according to any of the preceding claims, wherein the chiral iridium catalyst has the general formula (Va), (Vb), (Via) or (Vlb): Qfrfrenn / zznz / E / Yii where R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenanthryl or phenyl, wherein 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenanthryl and phenyl are either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-alkyl, C1-C4 haloalkyl and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five C1-C4-alkyl substituents, R7 and R8 are independently of each other hydrogen or C1-C4-alkyl, R9 and R10 are independently selected from the group consisting of ethyl, isopropyl, sec-butyl, isobutyl, tere-butyl, cyclohexyl, cyclopentyl, adamantyl and benzyl, m is 1 or 2, R13 is isopropyl, sec-butyl, isobutyl, tere-butyl, phenyl or benzyl,R14 and R15 are independently selected from each other from the group consisting of Ci-Ce-alkyl and Ce-aryl-Ci-C4-alkyl, wherein the Ce-aryl in the Ce-Cu-aryl-Ci-C4-alkyl moiety is either unsubstituted or substituted with one to five substituents selected from the group consisting of halogen and Ci-C4-alkyl; R16 and R17 are independently selected from each other from phenyl, 1-naphthyl, or 2-naphthyl, each of which is either unsubstituted or substituted with one to five substituents selected from the group consisting of halogen, C1-C4 alkyl, and Ci-C4-haloalkyl; and R18 is phenyl, which is either unsubstituted or substituted with one to five substituents selected from fluorine and Ci-C4-haloalkyl.

13. The process according to claim 12, wherein R6 is selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tert-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 1-naphthyl, 9-anthracenyl, 2,4,6-triisopropylphenyl, 9-phenanthryl, or 2,6-diethyl-4-methylphenyl, R7 is hydrogen, R8 is hydrogen or methyl, R9 and R10 are equal and tere-butyl, categorically, cyclopentyl, or cyclohexyl, R13 is tert-butyl, R14 and R15 R16 and R17 are independently of each other phenyl, which is substituted by one or two methyl groups, in particular R16 and R17 are the same and 2-methylphenyl or 3,5-dimethylphenyl, and R18 is 3,5-bis(trifluoromethyl)phenyl.

14. The process according to any of claims 1 to 12, wherein the chiral iridium catalyst comprises a chiral ligand of formula (IIIa) or (IIIb), wherein R6 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 9-anthracenyl, 9-phenanthryl, or phenyl, which is either unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C4-alkoxy, C4-alkyl, C4-haloalkyl, and phenyl, wherein the phenyl is again either unsubstituted or substituted by one to five C4-alkyl substituents, R7 and R8 are independently of each other hydrogen or C4-alkyl, R9 and R10 are independently of each other selected from the group consisting of ethyl, isopropyl, sec-butyl, iso-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl and benzyl, and m is 1 or 2.

15. The process according to claim 14, wherein R6 is selected from the group consisting of phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tere-butylphenyl, 4-methoxyphenyl, 3,5-bis-tert-butyl-4-methoxyphenyl, 4-tere-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 1-naphthyl, 9-anthracenyl, 2,4,6-triisopropylphenyl, 9-phenanthryl, or 2,6-diethyl-4-methylphenyl, R7 is hydrogen, R8 is hydrogen or methyl, R9 and R1 are water and tere-butyl, cyclopentyl, or cyclohexyl, and M is 1.

16. The process according to any of claims 1 to 15, wherein the amount of additive used is within the range of 0.1 to 10 mol%, based on the amount of the compound of formula (II).