Patent ID: 8426617

Claim:
Process for the manufacture of a compound of the formula I wherein the position labelled with the asterisk is an asymmetry center and R 1 is a group of the formula with R 2 being a hydroxyl group or a protected hydroxyl group, and R 3 and R 4 being independently from each other hydrogen or methyl, and n being an integer from 1 to 10, comprising the step of hydrogenating a compound of the formula II wherein at least one carbon-carbon double bond is present, and wherein the dotted lines represent the possible positions of such (facultative) carbon-carbon double bonds; and R 1 and n are as above, in the presence of a chiral iridium (Ir) complex as the catalyst selected from the group consisting of Ir complexes of the formula III, IV, V, VI, VII, VIII, IX, X, XI or XV, and their enantioners of formula: wherein R, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 and X 22 are independently from each other hydrogen, C 1-4 -alkyl, C 5-7 -cycloalkyl, phenyl, phenyl substituted with one to three C 1-4 -alkyl, C 1-4 -alkoxy and/or C 1-4 -perfluoroalkyl groups, benzyl, 1-naphthyl, or ferrocenyl, the anion Y is a weakly coordinating anion, n is 1 to 2, and “o-Tol” means ortho-tolyl, “Ph” means phenyl, “TBDMS” means tert-butyl-dimethylsilyl, “p-Tol” means para-tolyl, “BAr F ” means tetra(3,5-bis(trifluoromethyl)phenyl)borate, and the Ir complexes of the formula III to XI and XV, and the corresponding enantiomeric formula whereby the cyclooctadiene ligand is replaced by ethene or norbornadiene.