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

Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62%—quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.