Ag(I)/SEC-AMINE-AMIDPHOS-CATALYZED ENDO-STEREOSELECTIVE SYNTHESIS OF FULLY SUBSTITUTED PYRROLIDINES VIA 1,3-DIPOLAR CYCLOADDITION BASED ON AZOMETHINE YLIDES

摘要

Cooperative catalysis using multifunctional organic scaffolds in combination with transition-metal ions is emerging as a powerful tool in asymmetric synthesis. In this report, a series of multifunctional amidophosphanes derived from substituted 1,2-benzenediamine or 2-aminobenzylamine and chiral a-amino acids, in combination with silver(I) salts, have been developed to cooperatively catalyze the azomethine ylides-involved 1,3-dipolar cycloaddition with maleates. Under optimal conditions, fully substituted endo-pyrrolidines were obtained in high to excellent yields (up to 92% yield) and enantioselectivities (up to 94% ee).