The reaction of vinylsulfonamides with donor-acceptor carbenes derived from a-aryldiazoesters, catalyzed by the tert-butyl glycine-derived dirhodium complex Rh-2(S-4-Br-NTTL)(4), has been reported. This method provides a variety of alpha-aryl-beta-aminocyclopropane carboxylic acid derivatives bearing one quater-nary carbon stereogenic center vicinal to the amino-substituted carbon in high yields with excellent diastereo- and enantioselectiv-ities. Vinylsulfonamides showed complementary advantages over the well-developed vinylamides or vinylcarbamates for this Rh(II)-catalyzed cyclopropanation strategy. Moreover, these conformationally restricted alpha-aryl- beta-aminocyclopropyl carboxylic acid derivatives can be readily incorporated into dipeptides.