Chiral N-phosphoryl imines: design, synthesis and direct asymmetric addition reactions with diketones and diesters

(S)-BINOL-based chiral N-phosphoryl imines have been designed and synthesized. These N-phosphoryl imines have been proven to be efficient for direct 1,2-addition reaction with both cyclic and linear diketones without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. The absolute configuration has been unambiguously determined by converting a product into an authentic sample.