A Chiral Secondary Amine-Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions

A class of multifunctional amidophosphanes derived from chiral 1,2-diphenylethylenediamines and natural -amino acids has been developed. Among these, in combination with silver(I) salts, a chiral secondary amine-amidophosphane precatalyst has been demonstrated as being a highly efficient multifunctional precatalyst in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides, including a series of heterocyclic, aliphatic, and 2-substituted azomethine ylides, and aromatic ,-unsaturated aldehyde derived imino esters with different electron-deficient alkenes, as well as the three-component reaction of -imino esters generated in situ by using N , N -diisopropylcarbodiimide as dehydrating agent. Under optimal conditions, highly functionalized endo -adducts were obtained in high to excellent yields (up to 99% yield) and enantioselectivities (up to >99.9% ee).