Chiral phosphorus compounds, a process for their manufacture and their application to the catalysis of enantioselective synthesis reactions

A method of using a chiral phosphorus-containing ligand comprising at least one amine radical and at least one dihydrocarbylphosphinoxy radical of the formula W=OP(R).sub.2, in which R is a hydrocarbon radical selected from the group consisting of alkyl, aryl, and cycloalkyl radicals, wherein said ligand is selected from the group consisting of:

• those of the formula ##STR18## those of the formula ##STR19## those of the formula ##STR20## and those of the formula ##STR21## in which formulae:
• R.sub.1 and R.sub.2 are selected from the group consisting of a hydrogen atom and hydrocarbon radicals selected from the group consisting of alkyl, aryl, and cycloalkyl radicals;
• R.sub.3 and R.sub.4, which must be different from one another, are selected from the group consisting of a hydrogen atom and hydrocarbon radicals selected from the group consisting of alkyl, aryl, and cycloalkyl radicals that may or may not carry at least one functional group selected from the group consisting of the alcohol, thiol, thioether, amine, imine, acid, ester, amide, and ether functional groups;
• and
• R.sub.5 and R.sub.6 are selected from the group consisting of hydrogen atoms and hydrocarbon radicals selected from the group consisting of alkyl, aryl, and cycloalkyl radicals that may or may not contain functional groups;
• in a hydrogenation reaction for the synthesis of optically active organic compounds, comprising reacting one or more unsaturated organic compounds that do not possess a center of asymmetry with (A) one or more transition metal complexes of the formula MZ.sub.q, wherein M is a metal of group VIII of the Periodic Table, q is the degree of coordination of the metal M, and Z is an atom or molecule capable of complexing the metal M and (B) one or more of said chiral phosphorus-containing ligands, said hydrogenation reaction being carried out at temperature of between -50.degree. and +200.degree. C. and under a pressure of between 1 and 200 bars.