'Royal College of Obstetricians & Gynaecologists (RCOG)'
Abstract
The introduction of two nonequivalent diarylphosphanyl
substituents into the 2- and 2'-positions of 1,1'-binaphthalene
has been successfully accomplished in four steps
from 1,1'-binaphthalene-2,2'-diol (BINOL) through conversion
into the ditriflate followed by sequential substitution of
triflate groups mediated by palladium or nickel catalysts. The
selective monosubstitution of the triflate has been achieved
by introducing the first phosphorated substituent in the form
of phosphane oxide through a Pd-catalyzed reaction. The otolyl-
substituted diphosphane 4c is a chiral inducer that is
more efficient than BINAP both in the Rh-catalyzed asymmetric
hydrogenation of acetamido acrylic acid derivatives
and in the Pd-catalyzed allylic alkylation of 1,3-diphenylprop-
2-enyl acetate (85% ee)