Process for the Preparation of Enantiomerically Pure 1-Substituted-3-Aminoalcohols

A process for the preparation of N-monosubstituted β-aminoalcohol sulfonates of formula

• wherein R1 is C6-20 aryl or C4-12 heteroaryl, each optionally being substituted with one or more halogen atoms and/or one or more C1-4 alkyl or C1-4 alkoxy groups, R2 is selected from the group consisting of C1-4 alkyl, C3-8 cycloalkyl and C6-20 aryl, each aryl optionally being substituted with one or more halogen atoms and/or one or more C1-4 alkyl or C1-4 alkoxy groups, and wherein R3 is selected from the group consisting of C1-18 alkyl, C6-20 cycloalkyl, C6-20 aryl and C7-20 aralkyl residues, comprising asymmetrically hydrogenating a β-aminoketone sulfonate of formula
• wherein R1, R2 and R3 are as defined above,
• in the presence of a base and a catalyst, the catalyst comprising a transition metal and a diphosphine ligand, at a hydrogen pressure of 5 to 50 bar, in a polar solvent, optionally in the presence of water.

β-Aminoketone sulfonates of the formula

• wherein R1 is C6-20 aryl or C4-12 heteroaryl, each optionally being substituted with one or more halogen atoms and/or one or more C1-4-alkyl or C1-4-alkoxy groups, R2 is C1-4-alkyl or C6-20 aryl, each aryl optionally being substituted with one or more halogen atoms and/or one or more C1-4-alkyl or C1-4-alkoxy groups and wherein R3 is selected from the group consisting of C1-18-alkyl, C6-20 cycloalkyl, C6-20 aryl and C7-20 aralkyl residues.

β-Aminoalcohol sulfonates of the formula

• wherein R1 is C6-20 aryl or C4-12 heteroaryl, each optionally being substituted with one or more halogen atoms and/or one or more C1-4-alkyl or C1-4-alkoxy groups, R2 is C1-4-alkyl or C6-20 aryl, each aryl optionally being substituted with one or more halogen atoms and/or one or more C1-4 alkyl or C1-4 alkoxy groups and wherein R3 is selected from the group consisting of C1-18-alkyl, C6-20 cycloalkyl, C6-20 aryl and C7-20 aralkyl residues.