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

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