The present invention relates to a chiral
iridium hydride complex comprising a) a chiral (P, N)-ligand and b) a stabilized
ketene ligand of formula (I), wherein R1 is selected from the group consisting of
hydrogen, a C1-C500-
alkyl group, a C2-C500-alkenyl group, a C1-C500-
alkoxy group, a C2-C500-alkenyloxy group, a C1-C500-alkylamino group, a C2-C500-alkenyl amino group, a di-(C1-C500-
alkyl) amino group, a di-(C2-C500-alkenyl) amino group, a N-(C1-C500-
alkyl)-N-(C2-C500-alkenyl) amino group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyloxy group, a C3-C8-cycloalkylamino group, a N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl) amino group, and a pharmaceutically acceptable salt thereof; a C6-C14-
aryl group, which may be substituted as further defined in the specification; r1a is selected from
hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, or R1a and R1 together with the
carbon atom to which R1a is attached and the carbonyl to which R1 is attached form a C5-C7-cycloalkanone ring wherein the C5-C7-cycloalkanone ring is unsubstituted or substituted by 1 to 4 substituents independently selected from C1-C6-alkyl and benzylidene, wherein the benzylidene group is unsubstituted or substituted by 1 to 5 substituents independently of one another selected from the group consisting of
halogen, a C1-C500-alkyl group, a C1-C500-
alkoxy group, a C1-C500-haloalkyl group, and a C1-C500-haloalkoxy group; r2 is selected from
hydrogen, a C1-C500-alkyl group, a C1-C500-
alkoxy group, a C1-C500-alkylamino group, a di-(C1-C500-alkyl) amino group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyloxy group, a C3-C8-cycloalkylamino group, an N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl) amino group, a C6-C14-
aryl group, which may be substituted as further defined in the specification; and arrow represents a bond attached to an
iridium atom; the present invention relates to chiral
iridium hydride complexes, and to a method for producing
optically active 4-substituted 1, 2, 3, 4-tetrahydroquinolines by enantioselective hydrogenation of the corresponding 4-substituted 1, 2-dihydroquinolines in the presence of such chiral iridium
hydride complexes.