Phosphoramidite-Phosphite Ligands for Allylic Substitution

Significance

This paper describes the preparation of a series of phosphoramidite-phosphite ligands and their use in Pd-catalyzed allylic substitution reactions. This is the first time that this type of ligand has been used for this type of reaction. A cooperative effect was noticed between the configuration at the C3-position of the tetrahydrofuran ring of the carbohydrate and the axial chirality of the biaryl moiety. Depending on the substrate, different configurations were shown to give optimal results. Allylic alkylations as well as aminations were shown to give relatively high selectivities.