Catalytic asymmetric reduction of enamines

A catalytic asymmetric reduction process, comprising the steps of:

• providing a catalytic amount of an active species of an enantiomerically enriched chiral catalyst selected from the group consisting of M(L)(L')(L"), M(L)(L')(L")(L'"), M(L)(L')(L")(L'")(L.sup.iv), and M(L)(L')(L")(L'")(L.sup.iv)(L.sup.v), where M is a group 3, 4, 5 or 6 metal, a lanthanide or an actinide, and L, L', L", L'", L.sup.iv, L.sup.v, independently, is any combination of H, alkyl, aryl, Si(R)(R')(R"), halogen, -OR, SR, or -NR(R'), PR(R')(R"), or a cyclopentadienyl group having the formula ##STR5## where R, R', and R" are H, alkyl, aryl, or silyl and are the same or different, and where R.sub.0, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrogen, alkyl, aryl, Si(R)(R')(R"), halogen, -OR, -SR,-NR(R'), PR(R')(R"), or -PR(R') groups in any combination, where R, R', and R" are as defined above:
• reacting an enamine substrate in the presence of hydrogen and the catalyst, the enamine substrate having the formula:
• ##STR6## where R is an alkyl group (saturated or unsaturated), an aryl group, a heteroaromatic group, or a substituted version thereof, and R.sub.1 and R.sub.2 are hydrogen, alkyl groups (saturated or unsaturated), aryl groups, heteroaromatic groups, except that R.sub.l or R.sub.2, or both R.sub.1 and R.sub.2, are not of the formula C(O)R.sub.3 ;
• and
• recovering and purifying an the reduced enamine reaction product having a high level of enantiomeric purity.