Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral pi-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.