An Ylide Transformation of Rhodium(I) Carbene: Enantioselective Three-Component Reaction through Trapping of Rhodium(I)-Associated Ammonium Ylides by β-Nitroacrylates

The chiral Rh-I-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and beta-nitroacrylates was achieved to obtain gamma-nitro-alpha-aminosuccinates in good yields and with high diastereo- and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of Rh-I-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of Rh-I-carbene-induced ylide transformation.