The interest in the preparation of enantiomerically pure compounds is
growing rapidly. In the last few decades tremendous progress has been
made in the development of efficient chiral ligands for the
metal-catalyzed asymmetric transformations. Currently, the asymmetric
catalysis has been extended over a practical scale and many of
industrial processes are carried out to produce chiral builing blocks.
This work involved the synthesis and the application of the new
D-glucosamine derived ligands. The relatively easy chemistry of the
sugars was a crucial advantage for the synthesis of amido-, imino-, and
amino-type phosphines. The ligands were obtained in a pure state and in
sufficiently large amounts in order to perform a series of
metal-catalyzed asymmetric reactions such as: allylic alkylation, Suzuki
cross-coupling and hydrogenation. The efficiency of mono- and disugar
based ligands was also investigated. The carbohydrate ligands have been
especially designed for the allylic alkylation purposes, and indeed,
they were the most active in this kind of reaction, inducing high
enantiomeric excesses. The systematic modification of the ligands
structure allowed the understanding that the key factor determining
their activity and enantioselectivity was the sugar skeleton.