P-chirogenic organophosphorus compounds

A process for producing a compound of formula (I)

• wherein
• R1 and R2 may be the same or different and represent each a substituted or unsubstituted group selected from alkyl, cycloalkyl, aryl, alkyloxy, cycloalkyloxy, aryloxy, alkylamino, cycloalkylamino, arylamino, and metallocenyl;
• R3, R4, R5, R6 may be the same or different and represent each a hydrogen atom or a substituted or unsubstituted group selected from the group consisting of alkyloxy, cycloalkyloxy, aryloxy, alkylamino, cycloalkylamino, and arylamino;
• E represents a substituted or unsubstituted group —BR9R10;
• wherein
• R9 and R10 may be the same or different and represent each an halogen, an hydroxyl, a substituted or unsubstituted group selected from the group consisting of alkyloxy, aryloxy, cycloalkyloxy, alkyl cycloalkyl and aryl;
• comprising
• (i) reacting chlorophosphine borane (VII)
• wherein R1 and R2 are as defined above,
• with a reagent RM, in which M is Li and R is an alkyl or an aryl group;
• and
• further reacting the product of this halogen-metal exchange with an aromatic compound of formula (VI)
• wherein X and Y may be the same or different and each represent F, Cl, Br, or I, and R3, R4, R5and R6 are as defined above,
• resulting in the corresponding P-chirogenic phosphine borane of formula (IV)
• wherein X, R1, R2, R3, R4, R5 and R6 are as defined above;
• wherein step (i) is carried out under cooling condition, at a temperature ranging from −110° C. to −10° C.;
• and
• (ii) performing two chemical transformations on compound (IV) leading to compound (I):
• a step (ii-a) of removing of the borane group and a step (ii-b) of coupling of an electrophilic reagent, which is a boronate reagent, on the ortho position;
• steps (ii-a) and (ii-b) being carried out in any order.