In this work, we introduced a multifunctional Ag(I)/CAAA-amidphos complex catalyzed asymmetric 1,3-dipolar cycloaddition of acrylates with α-imino esters, affording a series of 2,4,5-trisubstituted endo-pyrrolidines in good yields (up to 97%) with high enantioselectivities (up to 98% ee). Meanwhile, the catalytic system was also applied in the three-component one-pot reaction of α-imino esters formed in situ under the action of N,N′-diisopropylcarbodiimide. In addition, the gram-scale reaction was realized for the formal synthesis of (+)-ibophyllidine in eight steps.
We report the synthesis of 4-(furan-2-yl)-3,4-dihydro-2H-pyrrol-2-one derivatives. In this approach, two core structures, the furan ring and 3,4-dihydro-2H-pyrrol-2-one, are constructed via silver(I)-catalyzed cascade cyclization/cyclopropanation/ring-cleavage/nucleophilic substitution reaction of enynones with enamines. A reasonable mechanism has been proposed. This method possesses some advantages such as high chemoselectivity, mild reaction conditions, simple operation, and short reaction time.