Catalytic Asymmetric Desymmetrization of meso-Diamide Derivatives through Enantioselective N-Allylation with a Chiral π-Allyl Pd Catalyst: Improvement and Reversal of the Enantioselectivity

In the presence of the Trost ligands-Pd catalysts, N-monoallylation of bis(2,4,6-triisopropylbenzne)sulfonylamides derived from meso-1,2-diamines proceeds with good to excellent enantioselectivity (85-96% ee) to give asymmetric desymmetrization products. Under the same conditions, in the reaction with meso-bistolunesulfonylamide derivatives, reversal of the enantioselectivity is observed.