Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from d-glucosamine

The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been investigated. The results obtained and the NMR studies of free ligands and of their Pd-complexes obtained from dimer [(η3-C3H5)PdCl]2 revealed the mode of complexation and the influence of the configuration and of the nature of the substituent at the anomeric position on the enantioselectivity of the studied asymmetric allylic alkylation reactions.