| 主权项 |
1. A process of manufacturing a compound of formula (I-A) or (I-B) or an acetal or a ketal thereof from a mixture of E/Z isomers of compound of formula (I) or (II) or an acetal or a ketal thereof wherein Q stands for H or CH3 and m and p stand independently from each other for a value of 0 to 3 with the proviso that the sum of m and p is 0 to 3, and where a wavy line represents a carbon-carbon bond which is linked to the adjacent carbon-carbon double bond so as to have said carbon-carbon double bond either in the Z or in the E-configuration and where the substructures in formula (I) and (II) represented by s1 and s2 can be in any sequence; and wherein the double bond having dotted lines () in formula (I) or (II) represent either a single carbon-carbon bond or a double carbon-carbon bond;comprising the steps
a) separating the isomers having E-configuration from the isomers having Z-isomers in the mixture of isomers of compound of formula (I) or (II) or the acetal or ketal thereof; b) submitting the isomers having the E-configuration of compound of formula (I) or (II) or the acetal or ketal thereof to hydrogenation by molecular hydrogen in the presence of a chiral iridium complex of formula (III) having the S-configuration at the stereogenic centre indicated by *; c) submitting the isomers having the Z-configuration of compound of formula (I) or (II) or the acetal or ketal thereof to hydrogenation by molecular hydrogen in the presence of a chiral iridium complex of formula (III) having the R-configuration at the stereogenic centre indicated by *;and optionally step d)
d) combining the hydrogenated products of step b) and c); wherein n is 1 or 2 or 3, preferred 1 or 2; X1 and X2 are independently from each other hydrogen atoms, C1-4-alkyl, C5-7-cycloalkyl, adamantyl, phenyl (optionally substituted with one to three C1-5-alkyl, C1-4-alkoxy, C1-4-perfluoroalkyl groups and/or one to five halogen atoms)), benzyl, 1-naphthyl, 2-naphthyl, 2-furyl or ferrocenyl; Z1 and Z2 are independently from each other hydrogen atoms, C1-5-alkyl or C1-5-alkoxy groups; or Z1 and Z2 stand together for a bridging group forming a 5 to 6 membered ring; Y⊖ is an anion, particularly selected from the group consisting of halide, PF6−, SbF6−, tetra(3,5-bis(trifluoromethyl)phenyl)borate(BArF−), BF4−, perfluorinated sulfonates, preferably F3C—SO3− or F9C4—SO3−; ClO4−, Al(OC(CF5)4−, Al(OC(CF3)3)4−, N(SO2CF3)2−N(SO2C4F9)2− and B(C6F5)4−; R1 represents either phenyl or o-tolyl or m-tolyl or p-tolyl or a group of formula (IVa) or (IVb) or (IVc) wherein R2 and R3 represent either both H or a C1-C4-alkyl group or a halogenated C1-C4-alkyl group or represent a divalent group forming together a 6-membered cycloaliphatic or an aromatic ring which optionally is substituted by halogen atoms or by C1-C4-alkyl groups or by C1-C4-alkoxy groupsR4 and R5 represent either both H or a C1-C4-alkyl group or a halogenated C1-C4-alkyl group or a divalent group forming together a 6-membered cycloaliphatic or an aromatic ring which optionally is substituted by halogen atoms or by C1-C4-alkyl groups or by C1-C4-alkoxy groups;R6 and R7 and R8 represent each a C1-C4-alkyl group or a halogenated C1-C4-alkyl group;R9 and R10 represent either both H or a C1-C4-alkyl group or a halogenated C1-C4-alkyl group or a divalent group forming together a 6-membered cycloaliphatic or an aromatic ring which optionally is substituted by halogen atoms or by C1-C4-alkyl groups or by C1-C4-alkoxy groups; and wherein * represents a stereogenic centre of the complex of formula (III). |
