Enantioselective process for cycloalkenyl β-substituted alanines

A process for preparing an enantiomerically enriched cycloalkylene-substituted alanine compound having the structure:

• comprising the step of asymmetrically hydrogenating a dehydro amino acid compound having the structure:
• in a suitable reaction media in the presence of a catalyst having a transition metal moiety complexed to a chiral phosphine ligand wherein:
• n is 1, 2, 3, or 4,
• R is selected from the group consisting of hydrogen, alkyl, aryl and —COR4, R1 is selected from the group consisting of hydrogen, halogen, alkyl, aryl, alkoxy, aryloxy and —COOR4, and R2 is selected from the group consisting of hydrogen, alkyl and aryl groups, wherein each R4 is independently selected from the group consisting of alkyl and aryl groups;
• to prepare enantiomerically enriched cycloalkyene substituted alanine compounds having the structure of Formula (IA) or (IB):