Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1 '-binaphthyl-2,2 '-diamine as chiral catalyst ligandsfor the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes

Chiral trifluoromethanesulfonamide 4, diphenylphosphoramides 5 and 6, and p henylthiophosphoramide 7 were prepared from the reaction of trifluoromethan esulfonic anhydride, diphenylphosphinic chloride, and diphenylthiophosphini c chloride with (R)-(+)-1,1'-binaphthyl-2,2'-diamine, respectively. They we re used as catalytic chiral ligands in the asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) isopropoxide to gi ve the corresponding sec-alcohols with 43-54%, 13-22%, 30-34%, and 52-64% e nantiomeric excess, respectively. (C) 2000 Wiley-Liss, Inc.