NEW CHIRAL AMINOPHOSPHINES AND THEIR USE IN ASYMMETRIC CATALYSIS

Chiral aminophosphines 4, 5 and 8 were synthesized from 1 in 34%, 57% and 42% overall yield, respectively. The new ligands were investigated with respect to their efficiency in the allylic alkylation of 1,3-diphenyl-1-acetoxy-2-propene with sodium malonate, the cross-coupling reaction of phenethylmagnesium chloride with vinyl bromide, and asymmetric hydrogenations of unsatured mono- and dicarbonic acids. The highest asymmetric inductions were observed with 4 (dimethyl 1,3-diphenyl-allyl-propandioate, 96% e.e.) and 5 (N-acetylphenylalanine, 77% e.e.; methylsuccinic acid, 56% e.e., 3-phenyl-1-butene 47% e.e.).