PREPARATION OF OPTICALLY-ACTIVE BINAPHTHYLMONOPHOSPHINES (MOPS) CONTAINING VARIOUS FUNCTIONAL-GROUPS

Optically active 2'-diphenylphosphino-1,1'-binaphthyls (MOP's) having various functional groups, cyano, aminomethyl, methoxycarbonyl, carboxy, and hydroxymethyl, at the C2-position were prepared. A cyano group was introduced on the MOP skeleton by nickel-catalyzed cyanation of 2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl which is readily prepared from optically active binaphthol. Preparation of the MOP derivatives bearing carboxylic groups were achieved by palladium-catalyzed monocarbonylation of binaphthyl-2,2'-bis(triflate) followed by phosphinylation of the remaining triflate group.